Our Top 10 Rupert Holmes Songs list presents the best Rupert Holmes Songs like “Escape (The Pina Colada Song)” “Him,” and many more. Born on February 24, 1947, in Northwich, Cheshire, England, was David Goldstein. He was raised in a home whose father was a warrant officer for the United States Army who was stationed in the UK. He was also a bandleader for the military. Goldstein’s mother also came from a musical background. When he was six years old, the family moved to a northern suburb in New York City. This is where he’d grow up and fine-tune his talent as a musician as a clarinet player at the Manhattan School of Music. His brother, Richard Goldstein, became an opera singer as a baritone vocalist with the New York Gilbert and Sullivan Players and with the Metropolitan Opera. As for David Goldstein, he’d go on to become Rupert Holmes, the man behind a series of internationally acclaimed songs, including “Escape (The Pina Colada Song).”
Early Career and Family Life
At twenty-two years of age, Goldstein married Elizabeth (Liza) Wood Derifuss, a woman whom he grew up with as a childhood friend. While he pursued his music career, she was an attorney. The two had a daughter together, Wendy, but in 1986, when she was just ten years old, died suddenly. It was discovered she had a brain tumor that was undetected as she never displayed any symptoms that she was terminally ill. The couple also has two sons, Nick and Timothy. Nick has since become a filmmaker while Timothy struggles with autism. Despite the tragedy and challenges, Rupert and Liza remain together as a married couple.
The beginning of his career started off as a session musician that saw his first hit recording credited as Rupert Holmes in 1970 for “Jennifer Tomkins.” He, along with Ron Dante, performed together for a song that met with some legal complications before it was finally released. For Holmes, as a session musician, played the piano for the Cuff Links, as well as the Buoys. As a member of the Buoys, Rupert Holmes would experience his first international hit, “Timothy.” It was also during this time frame Holmes was credited for his songwriting as he wrote several jingles and pop tunes that were performed by an impressive roster of recording artists. That list includes The Drifters, The Partridge Family, The Platters, Barry Manilow, Wayne Newton, Dolly Parton, and Gene Pitney. It was also his songwriting material that served as the musical score for the 1970 Keenan Wynn western, Five Savage Men.
For Rupert Holmes, his breakthrough as a solo artist started with the release of his first album, Widescreen. It was a 1974 release via Epic Records. This is where he began to produce storytelling material that tapped into an orchestrated romance with enough wit and charm to win over a highly entertained audience. One such audience member was Barbra Streisand. She asked if she could record songs from it, which Holmes agreed to. This agreement marked the beginning of a successful recording career Holmes would experience as she used the music for the 1976 box office hit, A Star Is Born. Holmes was credited for arranging, conducting, and writing songs for six of Barbra Streisand’s studio albums.
At one point, Rolling Stone Magazine compared Rupert Holmes with Bob Dylan as an artist known for enough ingenuity to win over a captivated crowd as if it were an easy task to do. His production skills were so highly regarded that he was in high demand to do for other artists what he did for Barbra Streisand. Although he was busy collaborating with other recording artists, he didn’t forget about his own career as a soloist. In 1979, he recorded and released “Escape (The Pina Colada Song)” as a single from his fifth studio album, Partners in Crime. “Him” also came from the same album, which joined “Escape” as one of Holmes’s signature songs. After this, he’d have his third top twenty hit single as a solo artist with “Answering Machine.”
Rupert Holmes Legacy
The 1985 musical, The Mystery of Edwin Drood, marked Rupert Holmes’ professional debut as a playwright. It became a big hit on Broadway, as well as in New York City’s Central Park. Initially, it was an unfinished Charles Dickens novel before his death. For Holmes, he used his childhood memories of English pantomime shows for inspiration as he took it upon himself to bring forth a series of alternate endings for each character who was suspected of Edwin Drood’s murder. This approach left the audience casting votes on a different murderer each night. This effort won Holmes a Tony Award for the book and score. He also won a series of honorable mentions with the Drama Desk Awards. The success of The Mystery of Edwin Drood encouraged Rupert Holmes to write additional plays. Some were also musicals while others were not. Aside from taking a break after the 1986 death of his daughter, Holmes remained prolific in the entertainment industry.
In 1986, “You Got It All” became a major hit for The Jets, an all-woman pop group that benefited from the songwriting skills of Rupert Holmes. Despite his success as a solo recording artist, he still contributed as a composer, musician, and songwriter. Other artists such as Judy Collins, Susannah McCorkle, and Frank Sinatra Jr. have each been on the receiving end of Holmes’ contribution to what turned them into successful performers themselves. Throughout the 1980s and 1990s, Holmes performed in a series of cabarets and comedy clubs, often sharing autobiographical anecdotes that came with his music. Most of these performances were in New York City.
Say Goodnight, Gracie was a play Rupert Holmes wrote as a storyline looking upon the relationship shared between George Burns and Gracie Allen. The play starred Frank Gorshin and it was Broadway’s longest-running stage show and the third longest-running solo performance show in its history. It was nominated for Best Play in 2003 by the Tony Awards. The winner that year was Take Me Out by Richard Greenburg. In 1990, Accomplice joined the ranks of The Mystery of Edwin Drood as an Edgar Award winner. Two years later, Holmes’ Solitary Confinement set a new box office record at Kennedy Center before it began its run on Broadway. On its heels was Thumbs, which was regarded as the most successful play in Helen Hayes Theatre Company’s history.
Rupert Holmes later became an author after writing a book to Swango: The Theatrical Dance Experience. It was a Romeo and Juliet-inspired play that made its off-Broadway debut in 2002. After this, he collaborated on the musical, Curtains, after the death of Peter Stone and Fred Ebb. Stone was the original writer behind the book while Ebb was the lyricist. Holmes rewrote the book and contributed additional lyrics to its songs. As a play, it debuted on Broadway with a performance quality that earned it a 2007 Drama Desk Award for Outstanding Book of a Musical.
In the meantime, Rupert Holmes also managed to make time to create the television series, Remember WENN for American Movie Classics. In 1996, he wrote the theme song and all of its fifty-six episodes. He’s also published two novels, 2003’s Where the Truth Lies and 2005’s Swing. He’s currently working on his third, The McMasters Guide to Homicide: Murder Your Employer.
As a recording artist, Rupert Holmes has a total of sixteen released albums to his credit. He was also the featured vocalist behind 1983’s Lake Freeze – The Raccoons Soundtrack. The Raccoons was a Canadian-produced animated series that also had a few movies that were featured before, during, and after the run of this popular children’s program. The series was just as recognized for its music score as the characters.
Top 10 Rupert Holmes Songs
#10 – Loved By the One You Love
From the album, Full Circle, “Loved By the One You Love” was the first of two singles released from it in 1981. On the US Billboard Adult Contemporary Songs chart, it peaked as high as number thirty-five. It didn’t quite crack into the US Billboard Hot 100 as it fell just three notches shy. The beauty behind this love song seemed to serve as an autobiographical tale of Rupert Holmes’ own love life. His marriage to his wife, Liza, so far managed to stand the test of time since the two married in 1969. The love the two shared together as a couple has seen its fair share of ups and downs. This song seems to serve as a testimony that when you’re truly “Loved By the One You Love” there’s no other feeling quite like it.
#9 – At Our House
From the Lake Freeze: The Raccoons Soundtrack, “At Our House” was a single that was released in 1983. Although it didn’t appear on any official music charts, it joined the rest of the songs featured on the album as a favorable tune for what was the first televised special before The Raccoons officially became a series in 1985. In the first special, Lake Freeze, Rupert Holmes was also the voice behind Dan the Forest Ranger, a supporting character that served as the caretaker of the story’s Evergreen Forest.
#8 – Morning Man
“Morning Man” was a single Rupert Holmes released in 1980 from the album, Adventure. It was the first of three songs released from it and became a number twenty-one hit on the US Billboard Adult Contemporary Songs chart. On the US Billboard Hot 100, it peaked as high as number sixty-eight. It was also a number ninety-four hit in Australia. This easy-listening classic featured the start of the day of a woman visiting the apartment of the “Morning Man” to enjoy an interlude before the routine of another work day begins.
#7 – I Don’t Need You
“I Don’t Need You” became a number twenty-one hit on the US Billboard Adult Contemporary Songs chart, as well as a number fifty-six hit on the US Billboard Hot 100. It was released as a single in 1981 from his album, Adventure. This song served as a conclusion to the previous hit, “Him,” which was a 1980 release from the album, Partners in Crime. It served as notice to the love interest who cheated on him that he’s decided he no longer needs her in his life and would rather move on without her.
#6 – Terminal
In 1974, “Terminal” became the debut single released by Rupert Holmes as a solo recording artist. It came from his album, Widescreen, released by Epic Records. This song became incredibly popular in the Phillippines and has since been covered by many Filipino musical artists. This musical tale was about a family man from Wall Street meeting a woman at a bus terminal. After calling in sick so he could enjoy a day-long fling with her, it felt like a born-again experience. At one point, he considered pursuing a relationship with her but chose to go remain in the stagnate condition of his current life. Before the song is over, he realized all his fateful decision did was live the rest of his days out as a terminally ill man with what he felt was very little to live for.
#5 – Jennifer Tomkins (featuring Street People)
In 1969, he participated in a recording with Ron Dante to record the single, “Jennifer Tomkins.” It was a song that met with some legal issues as Dante, who was a member of the Cuff Links at the time. The song was supposed to be for the group’s second studio album but Dante was forced to drop out of the band as the recording studio also produced music for another group Dante was involved with, the Archies.
“Jennifer Tomkins” became a release on its own through a different studio name, Street People. This is not the same Street People group from the mid-1970s. The song became a hit as of January 3, 1970, and remained on the US Billboard Hot 100 for fifteen weeks where it peaked as high as number thirty-six at one point. This is not the same Street People of the mid-1970s group who also happened to cover “Jennifer Tomkins” themselves. This was the first official hit that credited David Goldstein as Rupert Holmes as a contributor. He was also the pianist behind the original recording.
#4 – Answering Machine
On the US Billboard Adult Contemporary Songs chart, “Answering Machine” became a number twelve hit after it was released as a single in 1980. It was the third and final song released from the album, Partners in Crime. On the US Billboard Hot 100, it peaked as high as number thirty-two. This was the final song in his recording career to become a top forty hit. For Rupert Holmes, it was a wedding proposal that was performed on an answering machine when he attempted to contact his love interest by phone.
As a romantic, easy-listening number, the message of “I love you” didn’t quite make it as the thirty-second-time limit was up. Her response was calling him back but also reaching his answering machine. Before she could give an answer to his marriage proposal, the thirty-second-time limit was up for her.
#3 – Timothy (featuring the Buoys)
When “Timothy” was released as a single that peaked as high as number seventeen when it was released during the first month of 1971. The subject matter of cannibalism featured in the song drew controversy at a worldwide level. In this musical story, there was a cave-in that had two survivors feed on “Timothy,” the third man that was trapped inside with them but was killed when the collapse occurred.
For Rupert Holmes, tapping into a controversial subject for a song served as a winning formula, despite the attempts made by radio stations to have the song banned. On the US Billboard Hot 100, it became a number seventeen hit. In Canada, it peaked as high as number nine. It became the best-known song performed by the Buoys. Although you will not find Holmes singing in “Timothy,” he was the pianist that contributed to the success of this thought-provoking ballad.
#2 – Him
On the US Billboard Hot 100, “Him” became the follow-up hit behind his first signature single, “Escape (The Pina Colada Song).” On the US Billboard Hot 100, it became a number six hit. Originally, this was supposed to be the lead single, but the record producers suggested otherwise. On the US Billboard Adult Contemporary Songs chart, “Him” peaked at number four.
It was also internationally recognized, peaking at number eight in New Zealand, number eleven in Belgium, and number eighteen in the Netherlands. In this musical tale, Rupert Holmes discovered the pack of cigarettes he’s smoking doesn’t belong to him. This gives cause to believe his lover is cheating on him with another man. Before the song is over, he reached the understanding he needs to confront the situation and force the woman to make a decision.
#1 – Escape (The Pina Colada Song)
“Escape (The Pina Colada Song)” was the first and only number one hit recorded and released by Rupert Holmes as a solo artist. When it was released in 1979, it became the final number one hit on the US Billboard Hot 100 for the year. It also peaked at number one in Canada. The ingenuity behind this song featured a bored man wanting to add more pizazz to his love life. After reading an ad from a woman seeking a man who seems to want the same thing, learns the man must like Pina Coladas. The irony behind the musical story was realizing the woman who placed the ad was his own girlfriend whom he sought to “Escape” from as he thought the romantic relationship he had with her was dead. When the two realize they have more in common with each other than they thought, the love between them was rekindled.
The blend of comedy and romance, along with the easy listening groove of this song earned a gold certification with the Recording Industry Association of America, as well as platinum with the British Phonographic Industry. Although “Escape” was released in late 1979, it was still a hit when 1980 rolled around. By the end of 1980, the popularity of this song made it the eleventh best-selling song. It’s also in the record books as the first pop song to become a number one hit in two different decades.
Top 10 Rupert Holmes Songs article published on Classic RockHistory.com© 2022
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