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Writing an article about the 20 most loved songs of all time is a pretty big undertaking. The reason is that we’re not narrowing this down to any particular genre. I’m not writing about the 20 most loved rock songs, or the 20 most loved country, Christmas, or R&B songs. You know what I’m saying. I’m writing an article based on the 20 most loved songs of all time. That’s a pretty tall task.
Now, of course, it’s just one man’s opinion, although I did talk about it with some of the other writers here on the website, and I had clear reasons for the songs I picked. It’s not based on website research or anything like that. The reasons why I picked these songs are quite simple.
I have lived the life of a musician. Not a rock star, but a regular, ordinary working musician who has made a living playing music. I started in my early twenties, playing in cover bands. I spent two decades performing in lounge bands, wedding bands, and rock bands. I’ve spent decades playing piano in bars, restaurants, and cafes. I’ve taught piano, of course, as so many working musicians do, and then I became a journalist, interviewing famous musicians and writing articles like this one. What I learned throughout my career as a working musician was to play the songs that people love the most. Because when you’re playing on a stage and you’re nobody, it’s the songs you play that get you paid. As long as you play them in tune.
Over the years I performed for the public, I learned which songs people loved most because they were the ones they asked me to play most. That was true whether I was playing in a rock band, one of the other types of bands I worked with, or performing as a solo piano player. People always requested a particular set of songs. Of course, as a piano player, people asked for more standards, more solo artists, hits by Elton John and Billy Joel, or old Broadway songs that eventually became jazz standards. When I played in rock bands, certain groups and songs always came up. Some requests came between sets, and others were shouted out by people in the crowd.
So, based on all my experience as a musician, a teacher, and a writer, I felt it would be fun to put together 20 of the songs that I think people love the most, regardless of genre, regardless of style, and regardless of time. Of course, there are way more than 20, but as a journalist, I’ve also learned to limit these articles to 20 songs for various reasons. It’s tough enough to get people to read even just a little of what I write. I hope you enjoy this list, and of course, let me know if you agree with some of the choices and which other songs you would add. Most of all, thanks for coming to the site. I’ve been doing this a long time, and hopefully, I’ll be doing it for a lot longer.
# 20 – Sweet Caroline – Neil Diamond
I thought this was a perfect one to open this list with because, no matter what sort of musical situation I’ve been in, whether it was a band or as a solo artist, this song was always requested. It comes and goes, and it’s been popular at certain times of the year for various reasons, but people just love this one. I’ve had people grab me, hug me, and kiss me while I’m singing this at the piano. This song really brings people together.
Neil Diamond released “Sweet Caroline” in 1969, and it became one of the biggest hits of his career, reaching number four on the Billboard Hot 100. It’s remarkable to think that more than half a century later, the song may be even more popular than when it first came out. Diamond wrote plenty of great songs, including “Cracklin’ Rosie,” “Song Sung Blue,” and “I Am… I Said,” but there’s something about “Sweet Caroline” that makes people want to sing together. You don’t even have to be a Neil Diamond fan to love this one.
The song found a second home at Fenway Park in Boston, where it became a tradition during Red Sox games. It had been played occasionally beginning in the late 1990s before becoming a regular part of the eighth-inning experience in 2002. Of course, the crowd doesn’t just sing the lyrics. Everybody adds those famous responses to the horn arrangement and chorus. It’s almost as if the audience has become part of the recording. And this isn’t limited to Boston. You hear the song at sporting events, weddings, parties, and celebrations worldwide.
The name also has an interesting story behind it. Diamond once explained that a photograph of a young Caroline Kennedy had inspired him. Years later, he said he’d written the song with his then-partner, Marcia Murphey, in mind, but he needed a name that fit the melody. Whatever the inspiration, I don’t think anybody really cares when the music starts. They just want to sing it. After all my years performing, I can’t think of too many other songs that have brought so many strangers together in such a joyful way.
# 19 – Scenes From An Italian Restaurant – Billy Joel
If I were going to include a Billy Joel song on this list, I think most people would assume it would be “Piano Man.” And that’s not a bad call because, yes, “Piano Man” is one of the songs that I’ve been asked to play most of my life. And I have to tell you, I kind of despise being called the piano man because I feel that’s Billy Joel’s spot. But I guess when you’re a male piano player and singer from New York playing in a lounge or a bar, it’s just what you’re going to get called.
I think people get tired of “Piano Man” pretty quickly, but there’s one they don’t seem to get tired of, and one that’s been requested just as much in my experience. That would be “Scenes from an Italian Restaurant.” It’s harder to play but a little easier to sing, so I’m always happier to play that one. It’s funny, though; people don’t always ask for it by name. They usually say Brenda and Eddie, or the song with the wine in the beginning.
Billy Joel included “Scenes from an Italian Restaurant” on his landmark 1977 album The Stranger. Amazingly, it was never released as a regular commercial single during the album’s original run, yet it became one of the most beloved songs in his entire catalog. Running more than seven minutes, the composition moves through several distinct musical sections, beginning with a gentle piano ballad, picking up into an energetic rock and roll passage, and eventually telling the story of Brenda and Eddie, the popular couple whose dreams don’t quite work out the way everyone expected.
What I love about this one is that it’s really several songs rolled into one, and somehow it all works. Billy Joel was writing about growing up, old friends, youthful romance, and what happens when life doesn’t turn out the way we imagined. That recording has so much Long Island and New York character, which makes it especially meaningful for those of us who grew up around here. From behind the piano, I learned that people didn’t just love the big hit singles. They loved the songs that reminded them of their own lives. And “Scenes from an Italian Restaurant” does that as well as almost any song I know.
# 18 – More Than A Feeling – Boston
No, not all the songs on this list are songs people asked me to play, or songs my musician friends were asked to perform. Some are just songs I know almost everybody loves. This band blew everyone away when they first arrived on the scene in the fall of 1976, and it was simply because of this song. This is one that you just don’t get tired of. I’ve hardly ever heard anybody say anything negative about it. One of the truly great rock songs of our time.
Boston’s self-titled debut album was released in 1976, and it sounded unlike almost anything else on rock radio then. The band’s driving creative force was Tom Scholz, an MIT-trained engineer who worked at Polaroid while developing much of the music in his home studio. That story has always fascinated me. Here was a guy working on these incredible recordings while still holding down a regular job, and he wound up creating one of the biggest-selling debut albums in rock history. The album eventually received certification for 17 million copies in the United States.
“More Than a Feeling” was written by Scholz and featured Brad Delp’s magnificent lead vocals. Released as the band’s breakthrough single, it reached number five on the Billboard Hot 100. The combination of those layered guitars, the acoustic introduction, and Delp’s soaring voice was something special. That song seemed to explode out of the speakers. And what a chorus. I don’t think there’s a rock fan alive who has heard this song and doesn’t recognize it immediately from those opening notes.
What I think has kept “More Than a Feeling” so popular is that it captures the emotional side of rock and roll without sacrificing any of the power. The lyrics deal with memories and the way music can bring somebody from your past back into your mind. That’s a feeling almost everybody understands. The guitar work is brilliant, the production is remarkable, and Brad Delp’s vocal performance is one for the ages. Put this on in a room full of classic rock fans and watch what happens. People start singing, and suddenly it’s 1976 all over again.
# 17 – Summer Wind – Frank Sinatra
“Summer Wind” was always one of Frank Sinatra’s most popular songs worldwide. However, it really seemed to take on new life when it appeared in the movie The Pope of Greenwich Village during the opening sequence, as Mickey Rourke was getting ready and putting on his cufflinks and tie. I noticed right away that people were requesting the song all the time. And quite frankly, I really love this one.
“Summer Wind” actually began as a German song titled “Der Sommerwind,” with music by Heinz Meier and original lyrics by Hans Bradtke. Johnny Mercer later wrote the English lyrics, and Frank Sinatra recorded his famous version in 1966 for the album Strangers in the Night. The arrangement was by Nelson Riddle, whose work with Sinatra produced some of the most magnificent recordings in the history of popular music. That opening orchestral passage is so beautiful that you almost know what song you’re hearing before Sinatra even begins singing.
The 1984 film The Pope of Greenwich Village, starring Mickey Rourke and Eric Roberts, used Sinatra’s recording to wonderful effect. I always thought the song fit the opening sequence perfectly. There was something about the combination of the music, the New York setting, and Rourke’s character getting ready for another day that made the recording feel almost cinematic in a completely new way. Sometimes a film can introduce a great old song to people who might never have paid attention to it otherwise. I think that happened with this one.
What makes Sinatra’s performance so special is the way he handles the memories of a summer romance that has drifted away. He doesn’t sound as if he’s begging for the past to return. He’s remembering it with that effortless confidence that only Sinatra seemed to possess. The melody is beautiful, the lyrics are filled with nostalgia, and the entire recording has an elegance that never goes out of style. It’s one of those songs I always enjoyed playing because I understood exactly why people kept requesting it.
# 16 – Sweet Child O’ Mine – Guns N’ Roses
In the late ’80s, I played in a band called Phase 4 on Long Island. We played seven nights a week, and we played a lot of tough rock clubs. I talk about the song “Free Bird” later on this list, but what happened in the late ’80s was a big change in what people were screaming for at clubs. Suddenly, everyone wanted to hear Guns N’ Roses. They were the biggest new rock band to come around in a long time. I thought these guys were going to be huge, and of course they did become huge. Sadly, fighting among themselves probably tarnished what could have been an even more incredible career, but who knows? What I do know is that in almost every club we played for a pretty long time, people were screaming for Guns N’ Roses, and it was because of this song.
“Sweet Child O’ Mine” appeared on the band’s 1987 debut album Appetite for Destruction. When the single finally reached number one on the Billboard Hot 100 in September 1988, it became the band’s first and only American number-one pop single. That’s quite something when you consider how many famous recordings Guns N’ Roses eventually released. The song opened with one of the most recognizable guitar riffs of the entire decade, played by Slash, followed by one of Axl Rose’s most distinctive vocal performances.
There’s an interesting story behind that guitar introduction. For years, the riff was described as a warm-up exercise or something Slash had been playing around with. Slash later explained that it wasn’t really a warm-up exercise, but a riff he had been developing while experimenting on the guitar. Axl Rose wrote the lyrics about his girlfriend at the time, Erin Everly, the daughter of Don Everly of the Everly Brothers. What emerged from those sessions was an extraordinary combination of hard rock power and a genuine love song.
I can tell you from experience that this song changed the atmosphere in rock clubs. It wasn’t just the young guys standing near the stage who wanted to hear Guns N’ Roses. Everybody knew this record. And when a band launched into that famous opening riff, there was an immediate reaction. It was a song that brought hard rock back into the mainstream in a major way. I still think it’s one of the greatest rock singles of the 1980s, and the fact that people continue to love it almost forty years later says everything you need to know.
# 15 – I Say A Little Prayer – Dionne Warwick
Like I said earlier, with some songs on this list, you just know people love them because all you’ve heard throughout your entire life is how much people love that particular song. And of course, I include myself in that group. Burt Bacharach wrote some really good songs, and that’s probably an understatement, but I always thought this was one of his best. It’s been covered by many different artists, but I think Dionne Warwick’s original recording stands on top of all of them.
“I Say a Little Prayer” was written by Burt Bacharach and Hal David and released by Dionne Warwick in 1967. The single reached number four on the Billboard Hot 100 and became another major success for one of the greatest songwriting partnerships in popular music history. Bacharach’s melodies were often much more complicated than they sounded, with unusual rhythmic changes and sophisticated arrangements. Yet when Dionne Warwick sang them, everything seemed perfectly natural. She had an incredible ability to make complicated songs sound simple and beautiful.
Aretha Franklin recorded her own version in 1968, giving the composition a completely different soul and gospel feeling. Her interpretation was also a major hit, and I know plenty of people who prefer it. That’s the great thing about music. Two extraordinary singers can take the same song and create two very different performances, and both can become classics. There’s no need to argue about which one is better. I simply have a special place in my heart for Dionne’s recording because that’s the one I fell in love with first.
Then, in 1997, the song found another audience through the film My Best Friend’s Wedding. There’s that wonderful restaurant scene where Rupert Everett’s character starts singing and the people around the table join in. I love that scene because it demonstrates exactly what this article is about. A song written decades earlier suddenly has an entire room singing together. It doesn’t matter that it wasn’t a new hit anymore. Everybody knew it, everybody loved it, and everybody wanted to sing along. That’s the kind of lasting connection that earns a song a place on this list.
# 14 – I Will Always Love You – Whitney Houston
When I was playing in lounge bands in the ’80s, everybody requested Whitney Houston. She was so big. Usually, it was for her song “Greatest Love of All,” which had originally been recorded by George Benson. But her recording of Dolly Parton’s “I Will Always Love You” just blew the clouds out of the sky. Everyone wanted to hear this one. Do you remember how big the song became? It seemed like you couldn’t go anywhere without hearing Whitney Houston singing it.
Dolly Parton wrote “I Will Always Love You” and first released it as a single in 1974. The song was inspired by her decision to move on professionally from her longtime musical partner and mentor, Porter Wagoner. Her original recording reached number one on the country charts, and she returned to the top of the country chart with a new version in 1982. It’s a wonderful piece of songwriting, and Dolly deserves enormous credit for creating a melody and lyric that could work so beautifully in completely different musical settings.
Whitney Houston recorded her version for the 1992 film The Bodyguard, and it became one of the biggest hit singles in music history. The record spent fourteen consecutive weeks at number one on the Billboard Hot 100. Produced by David Foster, Whitney’s recording begins with her singing completely alone, without any instrumental accompaniment. That opening was brilliant because it immediately placed the focus on one of the greatest voices the world had ever heard. Then the arrangement builds, and when she reaches those enormous final choruses, the performance becomes almost overwhelming.
From a working musician’s point of view, this was one of those songs everybody wanted to hear, but not every singer wanted to attempt. That’s because everybody in the room knew exactly how Whitney Houston sang it, especially those extraordinary high notes toward the end. And when the audience knows a performance that well, there’s nowhere to hide. But that’s also part of what makes the recording so loved. Whitney took a magnificent song and made it one of the defining vocal performances of all time. There was no way I could put together this list without including it.
# 13 – I Will Survive – Gloria Gaynor
In the old days, when we played clubs, especially some of the big-time city clubs, whenever the band took a break, the DJ would play music between sets. And I don’t think I ever saw a song get people onto the dance floor as quickly as this one did, especially the women. If we were putting together a list of the 20 most loved songs by women, this one might just be number one. I’m serious. The reaction to this record was always incredible.
“I Will Survive” was written by Freddie Perren and Dino Fekaris and released by Gloria Gaynor in late 1978. The funny thing is that it originally appeared as the B-side of a single called “Substitute.” But disc jockeys and club audiences quickly recognized that the real hit was on the other side of the record. The song became a massive success, reaching number one on the Billboard Hot 100 in 1979. It also won the Grammy Award for Best Disco Recording in 1980, the only year that particular category was presented.
I know a lot of rock fans hated disco during the late 1970s. There was an enormous backlash against the entire genre, and some of the hostility was pretty ridiculous. But when you were standing in a nightclub and watching what happened when “I Will Survive” came on, nobody was arguing about musical categories. People wanted to dance. And this song gave them something more than a great beat. The lyrics were about finding strength, moving on, and refusing to let somebody else destroy your confidence.
That’s why this song has survived long after the disco era ended. It became something of an anthem for anyone who had gone through a difficult relationship or faced an experience that left them feeling defeated. There is genuine emotion underneath that dance groove, and Gloria Gaynor delivers it beautifully. I’ve watched entire rooms sing this song at the top of their lungs. Sometimes it seems as if everybody knows every word. If you’ve ever worked in a nightclub, you understand immediately why this belongs among the most loved songs of all time.
# 12 – In The Mood – Glenn Miller
It’s kind of sad how songs like this are slowly disappearing from popular culture. There are now generations of people who really don’t know very much about this music. However, back in the ’80s, people still loved it. Everyone loved dancing to “In the Mood,” and it was always a big showstopper. Of course, we can’t forget how big the song was when it first came out and how enormous Glenn Miller’s popularity was. I guess in the 1980s the recording was only a little over forty years old. Now it’s more than eighty years old, and it’s not heard nearly as often. But if we’re looking at the span of a century, I think this has to be one of the most loved recordings of all time.
Glenn Miller and his orchestra recorded “In the Mood” in 1939, and it became one of the defining recordings of the swing era. The composition is credited to Joe Garland, although its familiar musical ideas had roots in earlier jazz and dance-band arrangements. Miller transformed the piece into an enormously popular big-band recording. That opening saxophone riff is one of the most recognizable instrumental introductions in American music history. You hear just a few notes, and you immediately know what’s coming.
Glenn Miller was one of the biggest musical stars of the early 1940s. During World War II, he led an Army Air Forces band that entertained military personnel and brought a little bit of home to soldiers serving overseas. Tragically, Miller disappeared in December 1944 while traveling across the English Channel. His recordings continued to sell, and the orchestra’s sound became permanently associated with the wartime generation. “In the Mood” was more than a dance record. It became part of the soundtrack of an entire period in American history.
What I remember most about playing this music was the way people reacted to it. Some of those older couples really knew how to dance, and once the band got going, they would fill the floor. There was a wonderful energy in watching people move together to a big-band arrangement. You don’t see as much of that anymore. But the fact that this recording could still pack a dance floor decades after it was released tells you just how special it was. I don’t think a list covering the most loved songs of an entire century would be complete without Glenn Miller’s “In the Mood.”
# 11 – The Way We Were – Barbra Streisand
I remember in high school, it seemed like every girl wanted to be Barbra Streisand. Well, at least every girl who wanted to sing, get onstage in front of her school, and become a big star. They were always singing Barbra Streisand songs. Barbra had that big an impact in the 1970s, and of course, she carried that success into the ’80s and beyond. I was originally going to put “Memory” on this list, but then I thought, no, this one is probably more loved. You have to have Streisand here. She was one of the biggest female singers of the 1970s, and “The Way We Were” was one of her signature songs.
“The Way We Were” was written by composer Marvin Hamlisch, with lyrics by Alan and Marilyn Bergman, for the 1973 film of the same name starring Barbra Streisand and Robert Redford. The movie was a tremendous success, and the song became an even bigger part of popular culture. It reached number one on the Billboard Hot 100 in 1974 and won the Academy Award for Best Original Song. The recording also became one of the defining adult contemporary ballads of the decade.
What I think makes this song so moving is the way it deals with looking back. Everybody has memories of people they once loved, places they used to go, and moments they wish they could experience just one more time. And Barbra Streisand had the voice to make all those emotions feel very real. She could sing with tremendous power, but on a song like this, it’s the quieter moments that really get to me. The melody is gorgeous, and the lyrics capture something that becomes more meaningful as we get older.
There were plenty of other Streisand songs that people loved to request, and her recording of “Memory” from Cats was certainly one of them. But I think “The Way We Were” reaches an even broader audience because almost everybody can relate to what the song is saying. It doesn’t matter whether you’re young and looking back at a first love or older and thinking about an entire lifetime. The song works. And that is why, after all these years, I still think it’s one of the most beloved recordings of all time.
# 10 – Tiny Dancer – Elton John
There are a lot of Elton John songs I could have included on this list. I was really leaning toward “Your Song” or maybe even “Candle in the Wind,” but I think this one is just more universally loved among so many different audiences. I love how it was revived in the film Almost Famous, which is a pretty old film now. I still think of it as a new movie, but it came out back in 2000. And this song just brings everybody together. That’s what I love most about it.
“Tiny Dancer” first appeared on Elton John’s 1971 album Madman Across the Water. The lyrics were written by Bernie Taupin, while Elton composed the music. Although the song is now considered one of Elton’s greatest recordings, it wasn’t a massive American hit when it was first released as a single, reaching only number 41 on the Billboard Hot 100 in 1972. The composition was inspired by Taupin’s experiences in California, with Maxine Feibelman, who worked with Elton’s touring organization and later married Taupin, often associated with the song’s imagery.
Then Cameron Crowe used “Tiny Dancer” in the 2000 film Almost Famous, and an entirely new generation discovered it. If you’ve seen the movie, you probably remember the scene on the tour bus. The characters have been arguing, and the atmosphere is miserable. Then the song starts playing, and one person begins singing. Before long, everybody on the bus is singing together. It’s one of my favorite scenes in the movie because it demonstrates how music can change the mood of an entire group of people in just a few moments.
From a piano player’s perspective, “Tiny Dancer” is also a wonderful composition. The melody takes its time developing, and the arrangement gradually builds toward that magnificent chorus. Elton’s piano playing is beautiful, and his vocal performance has that warmth and emotion that made his early records so special. I can understand why many fans love it even more than “Your Song” or “Candle in the Wind.” The fact that a song that barely reached the American Top 40 eventually became one of Elton John’s signature recordings tells you everything about its lasting appeal.
# 9 – God Only Knows – The Beach Boys
This was another tough choice. I was originally going to go with “Good Vibrations.” That’s a huge one, and everybody loves that song, but I think there’s a deeper love for this one. There’s something magical in the melody here. I loved how it was used during the opening credits of HBO’s Big Love. I thought it fit the show perfectly, and it probably introduced a lot of people to this song, and maybe even to the Beach Boys themselves, who might not have known much about them. Or maybe not. Either way, it was a wonderful choice.
“God Only Knows” was written by Brian Wilson and Tony Asher and released on the Beach Boys’ extraordinary 1966 album Pet Sounds. Carl Wilson sang the lead vocal, delivering one of the most beautiful performances in the band’s entire catalog. The recording was issued as the B-side of “Wouldn’t It Be Nice” and reached number 39 on the Billboard Hot 100. That’s almost hard to believe when you consider how highly the song is regarded today. It has become one of the most admired compositions of the 1960s, and Paul McCartney has been among the many musicians who have praised its beauty.
I think what makes “God Only Knows” so special is the way the melody seems to float. Brian Wilson created an arrangement filled with unusual instrumental combinations and extraordinary vocal harmonies, yet the final result sounds completely natural. Carl Wilson’s singing is gentle, sincere, and deeply emotional. There isn’t a single moment where the band seems to be trying too hard. Everything just falls perfectly into place. And that’s what a truly great composition does. It sounds simple even when the music behind it is remarkably sophisticated.
The song also found new audiences through films and television. It was used in the closing moments of Love Actually and became the opening theme for the early seasons of HBO’s Big Love, starring Bill Paxton. I thought that television opening was particularly beautiful. Brian Wilson died in 2025, but he left behind an astonishing body of music. Of all the great Beach Boys songs, I think “God Only Knows” may be the one that touches people most deeply. You don’t have to be a surfer, or even a rock fan, to fall in love with this one.
# 8 – Purple Rain – Prince
Do you remember how big Prince became when this film came out? He was already pretty big, having enjoyed success on MTV with songs like “Little Red Corvette” and “1999.” But there was no way he was as big then as he became when the film Purple Rain was released. This would become his signature song. And when he performed it at the Super Bowl, in the middle of that incredible rainstorm, it seemed like the whole world was holding hands. That’s the impact of a great song like this, and it’s one of the reasons why it’s on our most loved list.
In 1984, the film and album Purple Rain turned Prince into one of the biggest musical stars in the world. The soundtrack spent twenty-four weeks at number one on the Billboard album chart, while the single “Purple Rain” reached number two on the Billboard Hot 100. The film also won an Academy Award for its music. Prince was doing something extraordinary at the time, bringing together rock guitar, funk, R&B, pop, and a completely individual visual style. Nobody else sounded or looked quite like him.
Then came Super Bowl XLI in 2007. Prince performed during the halftime show in Miami while rain poured down over the stadium. You almost couldn’t have written a better scene for a movie. Here was Prince standing in the middle of this enormous event, playing “Purple Rain” while the weather seemed determined to become part of the performance. It’s still regarded by many fans as one of the greatest Super Bowl halftime shows ever. You can read more about that performance in our complete history of Super Bowl halftime performers.
What I love about “Purple Rain” is that it’s one of those recordings that belongs to everybody. Rock fans love the guitar solo. R&B fans love the emotion in Prince’s voice. Pop fans love the melody. And people who don’t usually pay attention to any of those categories can still be moved by the song. Prince died in 2016, but his music remains as powerful as ever. I can’t imagine a celebration of the most loved songs of all time without this one.
# 7 – Billie Jean – Michael Jackson
I really didn’t want to put a Michael Jackson song on this list for a lot of reasons. But since this is a history site, and we’re talking about the most loved songs of all time, I felt I couldn’t ignore this album or this particular recording. Of course, this was the song from that album that turned into something bigger than life. It became more than just a hit single. It became one of those moments when popular music seemed to change right before our eyes.
“Billie Jean” was released from Michael Jackson’s landmark 1982 album Thriller and reached number one on the Billboard Hot 100 in 1983, remaining there for seven weeks. Written by Jackson and produced by Quincy Jones and Jackson, the recording featured one of the most recognizable bass lines in popular music. That bass line is really the heart of the track. Before Jackson even begins singing, you know exactly what song you’re listening to. For musicians, that kind of instantly recognizable introduction is something special.
Then came the famous Motown 25 television special, recorded in March 1983 and broadcast in May, when Michael Jackson introduced millions of television viewers to his moonwalk during a performance of “Billie Jean.” That moment became part of popular culture almost immediately. The song’s music video was also an important breakthrough for Black artists receiving major exposure on MTV. It wasn’t just a successful record anymore. It had become a musical and visual phenomenon that influenced an entire generation of entertainers.
For dance bands, this was one of those songs that could fill a floor as soon as the opening groove began. But you had to get that rhythm right because everybody knew exactly how it was supposed to sound. The song had an unmistakable pulse, and Jackson’s vocal performance fit it perfectly. Whatever people may think about the controversies surrounding Michael Jackson, the historical impact of this recording is undeniable. “Billie Jean” was one of the defining songs of the 1980s, and its influence on popular music continues to be felt.
# 6 – Free Bird – Lynyrd Skynyrd
We may not have this one at number one on our most loved songs list, but if I were putting together a list of the most requested songs of all time, I think anybody who’s been alive for the past sixty years knows that if you’re in a club, or even at a concert, someone will always scream the words “Free Bird!” It just became part of our culture. And probably in every single club, lounge, or restaurant I’ve ever played, I’ve heard somebody scream that request at me. And I’ve always played it. It’s fun to play, especially the ending.
Lynyrd Skynyrd released “Free Bird” on their 1973 debut album, (Pronounced ‘Lĕh-‘nérd ‘Skin-‘nérd). Written by Allen Collins and Ronnie Van Zant, the song developed into one of the most celebrated Southern rock anthems of all time. The original studio recording is magnificent, but the extended live performance released on the 1976 album One More from the Road became especially important to fans.
From a working musician’s perspective, the ending is both the fun part and the challenge. You have to keep the energy going, and the musicians really have to know what they’re doing. But the reaction from the audience makes it worth the effort. When people start shouting for “Free Bird,” they’re not just asking for another song. They’re participating in a rock and roll tradition that’s been around for decades. I’ve never gotten tired of the enthusiasm people have for this recording. It’s one of the reasons I love being a musician.
# 5 – Stairway To Heaven – Led Zeppelin
I have to say that we all pretty much got tired of this song because it was so overplayed for such a long time. But it all started to fade away, and then one night Ann Wilson and her sister Nancy got onstage and performed it at the Kennedy Center in front of Robert Plant, Jimmy Page, and John Paul Jones. They brought tears to Plant’s eyes, which is something I think would be pretty challenging to do. Anyway, of course I’m putting the original recording here, but Ann brought this song back for many of us and reminded us just how much we loved it when it was first released.
“Stairway to Heaven” appeared on Led Zeppelin’s untitled fourth studio album in 1971. Written by Jimmy Page and Robert Plant, the composition was never released as a regular commercial single in the United States during the band’s original career, yet it became one of the most requested songs on FM rock radio. That’s a remarkable achievement. The song begins almost like a gentle folk ballad before gradually building into an enormous hard rock performance, ending with one of the most famous guitar solos in history.
It became so overplayed that it eventually turned into a joke. Guitar stores became famous for supposedly discouraging customers from repeatedly playing the opening passage, and the 1992 film Wayne’s World made the idea even more popular with its famous reference to a ban on playing “Stairway.” I understand the joke because there was a period when you couldn’t go anywhere without hearing somebody attempting to play those opening notes. But that’s also the price a song sometimes pays for becoming so beloved. Everybody wants to learn it.
Then came the extraordinary 2012 Kennedy Center Honors performance by Ann Wilson, Nancy Wilson, Jason Bonham, and the other musicians who joined them for the tribute. Seeing Robert Plant moved to tears was an unforgettable reminder of how powerful the song still was. Jimmy Page’s original arrangement and Robert Plant’s vocal performance had created something timeless. And once that tribute reminded everybody of the song’s beauty, it was almost as if all those years of overexposure no longer mattered. You remembered why you fell in love with “Stairway to Heaven” in the first place.
# 4 – As Time Goes By – Dooley Wilson
This one probably needs no explanation as to why it’s on this list. Once again, the old standards are starting to fade as the generations who grew up with them get older. But I remember it well, and everyone always wanted me to play this one. Casablanca was one of the greatest movies of all time, and this song was a major part of what made it so special. When somebody would ask for “As Time Goes By” at the piano, I always knew exactly what they wanted to hear.
“As Time Goes By” was written by Herman Hupfeld in 1931 for the Broadway musical Everybody’s Welcome. It was a successful popular song long before Hollywood discovered it, but it became immortal when Dooley Wilson performed it as Sam in the 1942 film Casablanca. Starring Humphrey Bogart and Ingrid Bergman, the movie used the song to connect its characters to a romantic past that they could never completely forget. The composition became so closely associated with the film that it’s almost impossible to think of one without the other.
There’s also one of the most famous misquoted lines in movie history connected to the song. People are always saying “Play it again, Sam,” but that exact line is never spoken in Casablanca. The characters ask Sam to play the song, but not in the way everybody seems to remember. I always thought that was funny, especially because the song became such a popular request for piano players. The American Film Institute ranked “As Time Goes By” as the second greatest movie song of all time, right behind “Over the Rainbow.”
For me, the beauty of this song is its simplicity. You don’t need a huge arrangement or an enormous vocal performance to make it work. The melody is beautiful, and the words speak about the things in life that never really change, especially love and the memories that come with it. I think that’s why people kept asking for it so many decades after the movie first appeared. It wasn’t simply nostalgia for Humphrey Bogart or Ingrid Bergman. It was nostalgia for the people and moments in their own lives. And there are very few songs that express that feeling as beautifully as “As Time Goes By.”
# 3 – Over The Rainbow – Judy Garland
This song reminds me of my grandmother. I don’t think I’m alone in saying that. Millions of people must have watched this movie for the first time with their grandparents. Just the sound of those opening notes brings me back. That’s what music does. It’s so important in our lives.
Not everything from the 1920s and 1930s has started to disappear from our culture. This film and this song have remained a constant presence for generations. Yes, this one had to be on the list. I don’t think there are many people who have never heard “Over the Rainbow,” even if they’ve never sat down and watched The Wizard of Oz from beginning to end. It’s one of those recordings that seems to belong to everybody.
“Over the Rainbow” was written by Harold Arlen and E. Y. Harburg for the 1939 film The Wizard of Oz, starring Judy Garland as Dorothy. The song won the Academy Award for Best Original Song and eventually became one of the most celebrated compositions in movie history. Amazingly, the studio considered removing it from the film because executives worried it slowed down the story. Can you imagine The Wizard of Oz without “Over the Rainbow”? It’s almost impossible to think about. The American Film Institute later ranked it as the greatest movie song of all time.
For many of us, the song is tied to childhood memories of watching The Wizard of Oz on television. There was a time when the movie was shown as a special event, and families would gather around the television to watch it. Judy Garland’s beautiful performance captured the imagination of generations of children and adults. The melody is filled with longing, but there’s also something hopeful about it. It’s a song about imagining a better place, and I don’t think that idea will ever stop connecting with people.
Over the years, countless artists have recorded the composition, including Israel Kamakawiwo’ole, whose beautiful ukulele-based interpretation introduced it to another generation in the 1990s. Many people call the song “Somewhere Over the Rainbow,” although its official title is “Over the Rainbow.” Whatever you call it, there is no denying its place in music history. I can’t think of many songs that have been loved by so many different generations, and I doubt there will ever be a time when Judy Garland’s original performance doesn’t move people.
# 2 – A Day In The Life – The Beatles
We could probably put just about any Beatles song on this list. It’s pretty much impossible to pick just one. My first thought was “Hey Jude,” and then I went to “Something,” and then “I Want to Hold Your Hand,” and then “Strawberry Fields Forever.” It was really tough to pick one Beatles song, so I thought I’d choose what I think many serious Beatles fans consider their greatest recording. I know there are plenty of people who would disagree with that choice, but that’s the fun of putting together a list like this.
“A Day in the Life” closes the Beatles’ extraordinary 1967 album Sgt. Pepper’s Lonely Hearts Club Band. The song combines separate musical ideas developed by John Lennon and Paul McCartney, with Lennon handling the main sections and McCartney contributing the contrasting middle passage. Producer George Martin helped turn those ideas into an extraordinary recording, featuring an orchestra building toward enormous crescendos. It was unlike anything most listeners had ever heard on a popular music album.
One of the things that makes the recording so remarkable is the way it ends. After all that incredible orchestral movement, the Beatles finish with a massive piano chord that seems to hang in the air forever. Several musicians struck the chord together on multiple pianos, and the recording engineers carefully raised the volume as the sound faded, allowing the resonance to continue for an extraordinary length of time. From a piano player’s perspective, I have always loved that ending. It’s such a simple idea, but the effect is unforgettable. There is something magnificent about the way all that musical complexity finally resolves into one enormous chord.
That’s what I think makes “A Day in the Life” one of the greatest recordings in popular music history. The Beatles were taking the possibilities of the recording studio and pushing them into entirely new territory, yet the song still communicates emotion and wonder. It’s ambitious without losing the human connection. I know many listeners might prefer the more immediately accessible Beatles hits, and I understand that. But for me, this recording represents everything that made the Beatles so special. Even after hearing it hundreds of times, I still get caught up in the arrangement, the voices, and that extraordinary ending.
# 1 – White Christmas – Bing Crosby
I’m pretty sure this is the biggest-selling song of all time, at least when we’re talking about traditional record sales. And this one just touched everybody’s heart. Once again, just like Over the Rainbow, this song brings me back to my youth, listening to my grandparents and parents talk about this song. I distinctly remember how much it meant to them. Especially the generation who lived through wartime, who lost so many loved ones or had family members serving overseas during Christmas. This song spoke to those people in a way that very few recordings ever could. And it still does. I don’t think there’s another song in history that has been loved by so many people for so many different reasons.
“White Christmas” was written by Irving Berlin and first recorded by Bing Crosby in 1942. It appeared in the film Holiday Inn, starring Crosby and Fred Astaire, and won the Academy Award for Best Original Song. The recording became an enormous success, reaching number one on the popular music charts during World War II. According to Guinness World Records, Crosby’s version has sold an estimated fifty million physical singles worldwide, making it the best-selling physical single in recording history. That’s an extraordinary accomplishment for a song that has remained part of our lives for more than eighty years.
What makes “White Christmas” so special is the emotional connection it had with people during World War II. Imagine being a young soldier thousands of miles away from home, wondering whether you would ever see your family again, and hearing Bing Crosby sing about the Christmases you remembered. It’s almost impossible to understand how powerful that must have been unless you lived through those years. The original recording became so popular that Crosby returned to the studio in 1947 to make another version because the original recording master had become worn from repeated use. The 1947 version is the one most people hear today.
Of all the songs on this list, this is the one I feel most confident placing at number one. Not simply because of the sales figures, although they’re remarkable, but because of what the song has meant to people over so many generations. It reminds us of family, childhood, home, and the people we love who may no longer be with us. It brings back Christmas mornings, old photographs, and memories of a world that sometimes seems very far away. And when you hear Bing Crosby’s gentle voice singing that beautiful melody, all those feelings come rushing back. That’s the power of a truly beloved song. And for me, that’s why “White Christmas” belongs at number one on our list of the 20 most loved songs of all time.
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