The top 10 Johnny Maestro & The Brooklyn Bridge songs wouldn’t be complete without the mention of “Worst That Could Happen.” Even though these New Yorkers were often deemed as one-hit wonders, there was more to these talents than one big hit that swept across the nation as a phenomenon. While none of their studio albums seemed to make much of an impression, their live musical performances did. Including “Worst That Could Happen,” Johnny Maestro & The Brooklyn Bridge produced a total of six hits between 1968 and 1970.
Building Bridges
Born on May 7, 1939, John Mastrangelo started his musical career as a lead singer for The Crests. From 1957 to 1968, the group enjoyed a successful run as recording artists, including a string of hits such as “16 Candles,” “Step by Step,” and “Trouble in Paradise.” Along the way, Mastrangelo underwent a series of minor stage name changes before finally settling on Johnny Maestro. After his run was done with The Crests, he sought to make a name for himself as a solo artist. While he was doing so, there was a New York-based group known as The Del-Satins.
They became a popular figure on The Clay Cole Show, a local dance party program that performed a series of recorded songs from 1959 until 1967. After losing Stan Zizka as their lead singer, the crew of The Del-Satins was on the hunt to find a suitable replacement. When they met Maestro, they offered him a chance to team up with them, but he turned it down, at least at first.
Maestro’s manager at the time, Betty Sperber, hosted a monthly Battle of the Bands talent search contest at a Long Island-based nightclub known as Cloud Nine. On one fateful evening in 1968, she brought Maestro to the club and had him perform as a guest star. He was backed by a group known as The Rhythm Method. What turned out to be a successful evening led to the combination of the talent pools of Maestro, the Del-Satins, and The Rhythm Method into one entity.
In response to criticism from the general manager of Sperber’s Action Talents, Alan White, Sperber formed an eleven-man group named The Brooklyn Bridge. Together, Johnny Maestro and The Brooklyn Bridge worked out a combination of harmonies and horns before signing up with Buddah Records. The group’s first single was “Worst That Could Happen.” Already recorded by The 5th Dimension, it became a big hit for the group, winning over a fan base both nationally and internationally.
After surpassing one million copies sold, the single became certified gold by the Recording Industry Association of America. By 1972, Johnny Maestro & The Brooklyn Bridge had become household names after selling over 10 million records and appearing on popular programs such as The Della Reese Show and The Ed Sullivan Show.
While the Brooklyn Bridge was at the height of its career, the roster shrank from eleven men to five. Each of the vocalists in the group had their own musical instrument, including Maestro. He played the rhythm guitar while Jim Rosica played bass. Going into 1985, the group would expand its lineup to eight. Since its start in 1968, the band has been identified as The Brooklyn Bridge, Johnny Maestro & The Brooklyn Bride, and The Bridge. Over time, the group has recorded and released 11 studio albums, 7 compilation albums, and a live album. In 2005, the Brooklyn Bridge was inducted into the Vocal Group Hall of Fame. This was followed by inductions into the South Carolina Music R&B Hall of Fame and the Long Island Music Hall of Fame in 2006.
Rocking the Bridge
Although Johnny Maestro is no more after passing away from cancer on March 24, 2010, his legacy continues through new and surviving members of The Brooklyn Bridge. His death was followed by another legend from the group, Fred Ferrera, who passed away due to cardiac failure on October 21, 2011. Their deaths prompted one of the original members of The Brooklyn Bridge to return. Joe Ruvio came back, along with a new lead singer, Roy Michaels. However, as of 2013, Michaels was replaced by Joe Esposito of Brooklyn Dreams fame. In 2020, the Brooklyn Bridge was rocked again with the sudden death of Les Cauchi on March 3, 2020. Like Maestro and Ferrera before him, he was part of the original lineup when the group got its start in 1968.
Top 10 Johnny Maestro & The Brooklyn Bridge Songs
#10 – Inside Out (Upside Down)
Written by Jimmy Rosica and Shelly Davis, “Inside Out (Upside Down)” was a song he recorded with his bandmates, Johnny Maestro & The Brooklyn Bridge. This became one of nine songs on the 1969 album The Second Brooklyn Bridge. While the album failed to gain much momentum among critics and fans, there was no denying the band’s musicians had talent. Opening with a jazzy number with rhythm and soul, “Inside Out” was a song that shifted away from the doo-wop style that initially made the group popular. The lyrics captured the topsy-turvy reality of everyday life and romance in a world that often seemed to be flipped upside down.
#9 – 16 Candles
Originally, “16 Candles” was recorded and released by The Crests in 1958, and it became a huge hit, peaking at number 2 on the US Billboard Hot 100. It also became a number four hit on what’s now referred to as the US Billboard Hot R&B/Hip-Hop Singles chart. This song was written by Luther Dixon and Allyson Kent and recorded by Maestro and his bandmates while he was still with The Crests. As Johnny Maestro & The Brooklyn Bridge, “16 Candles” became a big part of their musical act over the years. It remains a staple favorite today, as the new Brooklyn Bridge lineup continues to take its audience back in time by covering this, plus several other iconic classics that made the era of 1950s and 1960s rock music so great.
#8 – Day Is Done
“Day Is Done” was a single by Johnny Maestro & The Brooklyn Bridge released in 1970. It was the final song performed by the group that would become a hit on the US Billboard Hot 100, peaking at number 96. Written by Peter Yarrow, this classic was originally recorded and released in 1969 by his group, Peter, Paul, and Mary. It was an anti-war song against the Vietnam War that peaked at number 21 on the US Billboard Hot 100. The performance by Maestro and his crew was just as dramatic and harmonic as the original, but with an R&B flair that made the sound of “Day Is Done” their own.
#7 – Christmas Serenade
1989’s “Christmas Serenade” was a song recorded and released by Johnny Maestro & The Brooklyn Bridge on their EP, Christmas Is… This festive tune stood out as a favorite among fans, even though it wasn’t officially released as a single. It was written by Ira and Mitch Yuspeh, then first recorded by Maestro and his crew before The Doo Wop Project covered it as “Christmas in the City” in 2018. “Christmas Serenade” became a festive favorite as Maestro made his observations about what makes the Christmas season so great.
#6 – Down By the River
Released in 1970 as a single, “Down By the River” was a minor hit for Johnny Maestro & The Brooklyn Bridge, peaking at number 91 on the US Billboard Hot 100. It was their cover version of the 1969 Neil Young and Crazy Horse classic from the album Everybody Knows This Is Nowhere. While there is no comparison to Neil Young, the performance laid out by the New York-based group was no slouch, either. Where Neil Young rocked it as a folksy number, Maestro did so with an R&B flair.
#5 – Blessed Is the Rain
“Blessed Is the Rain” was released by Johnny Maestro & The Brooklyn Bridge as a single in 1969. It was on the A-side of the same record that featured “Welcome Me Love” on its B-side. It was a modest hit, reaching number 48 on the US Billboard Hot 100 and number 45 on the Canadian Top Singles Chart. This song, as well as “Welcome Me Love,” was written by Tony Romeo, the same songwriter behind the 1970 iconic hit, “I Think I Love You” by the Partridge Family. This beautiful song had Maestro at his vocal best, while The Brooklyn Bridge roster performed “Blessed Is the Rain” as if it were a biblical experience, with a wonderful dose of rhythm and soul.
#4 – Welcome Me Love
“Welcome Me Love” was a song released by Johnny Maestro & The Brooklyn Bridge in 1969 on the B-side of a record that featured another hit, “Blessed Is the Rain.” On the US Billboard Hot 100, it peaked at number 48, just like its predecessor. On the Canadian Top Singles Chart, it peaked even higher at number thirty-eight. This came about as “Blessed Is the Rain” was on the way out and “Welcome Me Love” was on the way in on both of the nation’s official music charts. This catchy classic featured Maestro focusing on his love interest, hoping she would welcome him with open arms to cure their mutual loneliness. While this may not have been a top hit on the music charts, it did become a fan favorite that became more popular over time, especially when performed live.
#3 – Your Husband, My Wife
When “Your Husband, My Wife” was first released as a single in 1969, the lyrics sparked controversy. This song revolved around infidelity during an era when such an act was heavily frowned upon by the general population of society at the time. Regardless, it was popular enough to become a number 46 hit on the US Billboard Hot 100, and it has stood the test of time as a classic.
Fans of good doo-wop style music simply enjoyed how well Johnny Maestro & The Brooklyn Bridge performed together in perfect harmony. Although extramarital affairs were extremely taboo to talk about at the time, it didn’t change the fact that they still happened. “Your Husband, My Wife” was an incredible love song about two people who desperately wanted to be together, but not at the expense of hurting their respective spouses.
#2 – You’ll Never Walk Alone
“You’ll Never Walk Alone” peaked as high as number fifty-one on the US Billboard Hot 100 when it was released by Johnny Maestro & The Brooklyn Bridge as a single in 1969. This was an original 1945 song, performed as a show tune in the Rodgers and Hammerstein musical Carousel.
The song was first performed as an act of encouragement in the movie, after the lead character was dying in his wife’s arms. It was later performed during a moving scene featuring the couple’s daughter’s graduation from school. It didn’t take long for “You’ll Never Walk Alone” to become a cult classic as it became an unofficial anthem for emergency workers, medical staff, and sports teams. This song was also covered by numerous artists. Either with a gospel-like approach or as a gentle, easy-listening pop tune, “You’ll Never Walk Alone” remains one of the music industry’s all-time classics.
#1 – Worst That Could Happen
“Worst That Could Happen” was a song written by Jimmy Webb, then recorded in 1967 by The 5th Dimension. The Magic Garden was an album that mostly featured songs written by Webb. In 1969, Johnny Maestro & The Brooklyn Bridge released a cover version that peaked at number 3 on the US Billboard Hot 100. The song was about a man having to contend with the heartache of losing a woman he loved because he chose not to build a life with her in the form of marriage.
In what he felt was the “Worst That Could Happen” to him, she left him to marry someone who was willing to give her what she wanted. The song stood out for its quote from the “Wedding March” by Felix Mendelssohn, as well as the Shakespearean comedy, A Midsummer Night’s Dream. In Canada, “Worst That Could Happen” became a number-one hit on the Canadian Top Singles Chart. It was also popular in New Zealand as it peaked as high as number sixteen on its official music chart. After selling over one million copies, “Worst That Could Happen” also became an RIAA-certified gold seller.
Feature Photo: Peter Potter, CC BY-SA 3.0 <http://creativecommons.org/licenses/by-sa/3.0/>, via Wikimedia Commons
Updated March 17, 2026
Top 10 Johnny Maestro & The Brooklyn Bridge Songs article published on Classic RockHistory.com© 2026
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