Hailing from Slough, Bennett and the Rebel Rousers came to the attention of Joe Meek, at that time an aspiring independent producer. With Meek at the controls the group cut four singles between 1961 and the summer of 1963, all of which sank without trace. Much of '62 and '63 was spent playing in Germany at venues such as the Star Club in Hamburg. Indeed, during one of the Hamburg trips he struck up a friendship with the Beatles which would prove beneficial a few years later. After Allen decamped to the Searchers, Bennett brought in Bobby Thompson from Kingsize Taylor & the Dominoes. Liverpool's renowned saxophonist, Howie Casey, was also with the band for a time.

In 1964 they were signed by Brian Epstein's NEM's agency on the recommendation of the Beatles and reached the Top Ten with "One Way Love". Subsequent releases flopped despite powerful vocal performances from Bennett himself.

Early in 1966 their paths crossed with the Beatles again when they were booked as an opening act on the fab four's final European tour. During that tour, the Beatles introduced Bennett to one of their new songs "Got To Get You Into My Life", which was going to be included on the "Revolver" album to be released later that year. Paul McCartney produced Bennett's version of the song. Released in the summer of '66 and reaching No. 6 in the British charts, the record was both the biggest and the last hit that Cliff Bennett & the Rebel Rousers had.

There followed numerous personnel changes before the band dissolved in 1968. Bennett then formed The Cliff Bennett Band. This outfit comprised of Bennett (vocals), John Bennett (trombone), Alan Drover (saxophone), Stuart Hamer (trumpet), Mick Green (guitar), Robin MacDonald (bass) and Frank Farley (drums). Green and Farley had earlier been members of Johnny Kidd & The Pirates and, together with MacDonald had been members of Billy J. Kramer's backing group, the Dakotas.

In the 70s Bennett formed Cliff Bennett's Rebellion and sang with Toe Fat and Shanghai before eventually retiring from music temporarily in the late 70's.

By the mid 80's, Bennett was leading a new version of the Rebel Rousers.