The Biggest Comebacks in Music History

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25. Gladys Knight And The Pips
> Comeback song: “Love Overboard”
> Entered Top 40: 1/30/1988
> Years between Top 40 hits: 12.1

Gladys Knight And The Pips emerged from African-American gospel tradition to record eight top 10 hits in the 1960s and 1970s. The Motown hit machine fell into a dry spell before returning to the Top 40 with “Love Overboard” in 1988, about 12 years after their previous Top 40 hit, “Part Time Love.”

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24. Enya
> Comeback song: “Only Time”
> Entered Top 40: 9/1/2001
> Years between Top 40 hits: 12.4

The Irish singer was a prominent voice of new age music, as a solo performer and a member of the group Clannad. Her career reached a high-water mark in 1989, when her atmospheric song “Orinoco Flow (Sail Away)” put her on the Billboard Hot 100 chart at No. 24. She wouldn’t return to the Top 40 until 2001, when her song “Only Time” rose to No. 10. More recently, Enya has collaborated with Mario Winans and P. Diddy on the song “I Don’t Wanna Know” that climbed to No. 2 in 2004.

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23. Dave Edmunds
> Comeback song: “Slipping Away”
> Entered Top 40: 7/30/1983
> Years between Top 40 hits: 12.4

It was about 12 years between Top 40 hits for the Welsh-born rockabilly singer. “Slipping Away,” in which he collaborated with former Electric Light Orchestra member Jeff Lynne, was the biggest hit for Edmunds since his greatest singles success, “I Hear You Knocking,” in 1971, which reached No. 4 on the Billboard Hot 100.

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22. Cliff Richard
> Comeback song: “Devil Woman”
> Entered Top 40: 8/14/1976
> Years between Top 40 hits: 12.5

The British pop star has had three top 10 hits on Billboard, and his biggest was his comeback effort “Devil Woman.” Richard’s last Top 40 success had been “It’s All In The Game,” in February 1964, just as the British invasion began.

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21. Conway Twitty
> Comeback song: “You’ve Never Been This Far Before”
> Entered Top 40: 9/15/1973
> Years between Top 40 hits: 12.6

The Mississippi-born Conway Twitty had 40 No. 1 hits on the country charts and sold more than 50 million records in the course of his career. In 1960, though, he scored two mainstream Top 40 hits, with “What Am I Living For” and “C’est Si Bon (It’s So Good) — a feat he didn’t repeat until almost 13 years later, with a song he wrote, “You’ve Never Been This Far Before.”