By the time he was a teenager, Bobby was playing drums in a dance band called Rocco And The Saints" that featured Frankie Avalon on the trumpet. The band played Summer bookings in the seaside resorts around Atlantic City. Rydell also played the guitar and bass and was a natural comedian. Frankie Day, who managed Rocco And The Saints, became interested in Rydell as a solo act. With Bobby's father's approval, Day began taking Rydell to different record companies. Day was unsuccessful for several years, though Rocco And The Saints had backed Frankie Avalon's first sessions on Chancellor Records.
In late 1958, Bobby recorded a song called "Fatty Fatty" for Veko Records in Baltimore. The release went nowhere, the promoters disappeared with the masters and Rydell's father was left with the bill for the sessions. Finally, Frankie Day approached Bernie Lowe, the owner of Philadelphia's Cameo Records, who had been Rydell's vocal coach when he was ten. In January 1959, Rydell signed a contract with Cameo and his first single "Please Don't Be Mad" was released in February, 1959. Unfortunately "Please Don't Be Mad" did no better than "Fatty Fatty". Lowe then got him a guest spot on Dick Clark's American Bandstand. He was only interviewed and didn't sing, but he did manage to plug "Please Don't Be Mad". In 1959, Cameo released his second single "All I Want Is You", but again the record saw little action. Rydell became discouraged as his old friend Frankie Avalon had been making hit records for over a year. "Venus" was one of the biggest hits of 1959 and even Fabian, who was never a strong vocalist, had been having hits since the first of the year.
Rydell had almost resigned himself to being a drummer in a second rate combo, when Bernie Lowe came up with a song called "Kissin' Time". Released in mid-June, the record caught on in Philadelphia, followed by Detroit and Boston. Dick Clark began playing it on American Bandstand, and within three weeks after its release,it was a national hit. Bobby Rydell was just seventeen In August, Rydell appeared on Bandstand again where he lip-synched "Kissin'' Time" and "We Got Love", which was a solid follow up. Rydell appeared at the Michigan State Fair in September, 1959 with a Dick Clark show. This led to him touring with Dick Clark's first Rock 'n' Roll caravan that began on September 18th and was booked for forty-four shows through the end of October. By then, "We Got Love" had gone Gold and become Bobby's first Top Ten hit when it reached #6.
Rydell's biggest selling single, the million selling "Wild One" was released in early in 1960. It shot to #2 during a thirteen week stay on Billboard's Top 40. After "Little Bitty Girl" made it to #19, "Swingin' School" became a springtime #5 hit and a third million seller. That Summer, Bobby showed off his powerful voice on an song called "Volare". The tuned had been pulled from a previous session of songs that were recorded in a big band style, meant to introduce Rydell to an older audience. Over the next three years, Rydell had a string of hits that sold more than a half million copies each. Several, including "Sway" (#14), "Good Time Baby" (#11), "I've Got Bonnie" (#18), "I'll Never Dance Again" (#14), "The Cha-Cha" (#0), and "Wildwood Days" (#17) made the Top Twenty. 1963's "Forget Him" soared to #4 and sold over a million copies. Along with making hit records, Rydell appeared in the 1963 version of the Broadway hit musical Bye, Bye, Birdie. Though the story dealt with a Rock 'n' Roll singer, Rydell was cast with Ann-Margaret as a pair of high school sweethearts.
In 1964, the so-called British Invasion began and Rydell, like many American acts, was shut out from the hit making machinery of the record business. Receiving a draft notice, Rydell tried to get out of service as a hardship case. He wrote to the board that his father worked for him and was the sole means of support of his grandparents that lived with him. When the request was denied, Rydell joined a local Philadelphia National Guard unit. His career was interrupted for six months of basic training in 1964.
Rydell signed with Capitol Records, but never did anything of interest. In 1969 he signed with Reprise, a label founded by Frank Sinatra. His first single, "Lovin' Things" with "It's Getting Better" on the flip side, received no promotional support. "Lovin' Things" was covered by The Grassroots and "It's Getting Better" by Mama Cass, and each became a mid-size hit. His next single, "The River Is Wide" went nowhere, but The Grassroots version moved up the charts to #31. After three more singles failed to crack the Hot 100, Rydell packed it in. Rydell went on to join the Rock 'n' Roll revival shows at Madison Square Garden. In the '70s he was a popular entertainer at Hugh Hefner's Playboy Clubs. He also worked at the Hyatt Regency and Waldorf Hotel chains and appeared at Disney theme parks. In the late '70s, Bobby tried moving into a Pop direction pioneered by Barry Manilow, but met with little success. He appeared in a Summer stock of Bye, Bye, Birdie, this time playing the part of the father. He also appeared in a failed pilot comedy-variety television show, One More Time that was to be produced by The Osmonds.
In the Summer of 1985, Rydell joined his old friends Frankie Avalon and Fabian on the Boys Of Bandstand tour and for the next few years performed in clubs all over the world. He also appeared on a number of Dick Clark television specials, recalling the early days of Rock 'n' Roll. In 2000, Bobby released a new album called "Now and Then", made up of re-makes of his old hits and some new material. It was his first new album in over twenty years. He has continued to tour the world and his 2012 schedule was booked solid with appearances across America with The Golden Boys and in Australia as a solo act. Those touring plans were interrupted when the 70-year-old singer underwent a liver and kidney transplant in early July. In January 2013, six months after double transplant surgery, Rydell returned to the stage in Las Vegas for a three night engagement to a sold out audience. He continued to perform internationally and returned to tour Australia in 2014. In 2017, his website still showed a handful of bookings with The Golden Boys at various locations in the United States.
Billboard magazine listed Bobby Rydell as earning twelve U.S. Top 40 hits, making him one of the top five artists of his era.
For more, be sure to read Gary James' Interview With Bobby Rydell