25. 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.
24. 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) â a feat he didn’t repeat until almost 13 years later, with a song he wrote, “You’ve Never Been This Far Before.”
23. Donny Osmond
> Comeback song: Soldier Of Love
> Entered Top 40: 4/15/1989
> Years between Top 40 hits: 12.7
Performing since he was a child, Donny Osmond had his first hit records, both as a solo artist and as part of his family group, The Osmonds, in 1971, when he was barely in his teens. He had 11 Top 40 hits in all up through his 1976 release of “C’mon Marianne” but then had to wait until 1989 to repeat the achievement.
22. Jimmy Ruffin
> Comeback song: Hold On To My Love
> Entered Top 40: 3/22/1980
> Years between Top 40 hits: 12.9
“Gonna Give Her All the Love I’ve Got” was an early hit for Motown star Ruffin, older brother of David Ruffin of The Temptations. But while he had three more Top 100 songs in the late 1960s and early ’70s, he didn’t reach the Top 40 again until 1980.
21. Kylie Minogue
> Comeback song: Can’t Get You Out Of My Head
> Entered Top 40: 2/9/2002
> Years between Top 40 hits: 13.0
Australian actress-turned-singer Kylie Minogue had 13 singles in the U.K. Top 10 in the late 1980s and early ’90s but has gotten less love from U.S. listeners. Minogue has reached the top 10 on the Billboard Hot 100 only twice. Her last appearance in the Top 40 before her comeback song was with “It’s No Secret” in 1989 that peaked at No. 37.