Whether it’s in motion pictures, sports, or the media, nothing is more capricious than fame. Frank Sinatra voiced that sentiment in the song “That’s Life,” when he sang, “You’re ridin’ high in April, shot down in May” – though he promised to be “back on top in June.”
For some music artists, it has taken a lot longer than a few months to get back on top. To determine the biggest comebacks in music history, 24/7 Tempo identified the artists with the longest periods of time between singles consequently entering the American Top 40 chart – comprising the top 40 spots on the Billboard Hot 100 popular singles chart.
To be considered for our list, an artist’s “comeback song” had to be a new release at the time it entered the chart. Older releases that became popular again years later were not included. Songs on which an artist was prominently featured, though not the headliner, are considered to be one of that artist’s hits if they are listed under the artist’s name by Billboard. (Here are some famous musicians who never topped the Billboard Hot 100.)
In the music industry, it is not uncommon for artists who had a string of hits to suddenly lose an audience – such as British Invasion groups like the Dave Clark Five, because of the whims of the teenage audience. Other artists fell out of favor because tastes change, or they hit a creative roadblock and didn’t produce material that excited the public.
But some persevered by recreating their image or collaborating with younger performers to regain the spotlight. An example of the latter is country singer Billy Ray Cyrus. He had a solo hit with “Achy Breaky Heart” in 1992, and in 2008, he had a comeback hit with the song, “Ready Set, Don’t Go,” with an assist from his daughter Miley – and was part of another smash hit in 2019 on the remix of “Old Town Road” by Lil Nas X. (Interested in older hits? Here’s the most popular song the year you were born.)
Click here to see the biggest comebacks in music history
Though not all the artists on the list are well known, you might be surprised at the droughts experienced by some of the more famous performers in their careers.
65. Peaches & Herb
> Gap between Top 40 hits: 11 years
> Comeback song: Shake Your Groove Thing (1979)
> Prior Top 40 hit: Two Little Kids (1968)
> Career Top 40 hits: 8 songs (66 weeks total)
[in-text-ad]
64. Peggy Lee
> Gap between Top 40 hits: 11 years
> Comeback song: Is That All There Is (1969)
> Prior Top 40 hit: Fever (1958)
> Career Top 40 hits: 2 songs (17 weeks total)
63. Herb Alpert
> Gap between Top 40 hits: 11 years
> Comeback song: Rise (1979)
> Prior Top 40 hit: This Guy’s In Love With You (1968)
> Career Top 40 hits: 19 songs (124 weeks total)
62. James Brown
> Gap between Top 40 hits: 11 years, 3 months
> Comeback song: Living In America (1986)
> Prior Top 40 hit: Papa Don’t Take No Mess (Part I) (1974)
> Career Top 40 hits: 44 songs (250 weeks total)
61. Lulu
> Gap between Top 40 hits: 11 years, 5 months
> Comeback song: I Could Never Miss You (More Than I Do) (1981)
> Prior Top 40 hit: Oh Me Oh My (I’m A Fool For You Baby) (1970)
> Career Top 40 hits: 4 songs (36 weeks total)
60. Ben E. King
> Gap between Top 40 hits: 11 years, 6 months
> Comeback song: Supernatural Thing – Part I (1975)
> Prior Top 40 hit: I (Who Have Nothing) (1963)
> Career Top 40 hits: 6 songs (61 weeks total)
59. Yes
> Gap between Top 40 hits: 11 years, 7 months
> Comeback song: Owner Of A Lonely Heart (1983)
> Prior Top 40 hit: Roundabout (1972)
> Career Top 40 hits: 6 songs (43 weeks total)
[in-text-ad-2]
58. Bad Company
> Gap between Top 40 hits: 11 years, 7 months
> Comeback song: If You Needed Somebody (1991)
> Prior Top 40 hit: Rock ‘n’ Roll Fantasy (1979)
> Career Top 40 hits: 9 songs (64 weeks total)
57. Tom Jones
> Gap between Top 40 hits: 11 years, 8 months
> Comeback song: Kiss (w/ The Art of Noise) (1988)
> Prior Top 40 hit: Say You’ll Stay Until Tomorrow (1977)
> Career Top 40 hits: 18 songs (142 weeks total)
56. Al Green
> Gap between Top 40 hits: 11 years, 11 months
> Comeback song: Put A Little Love In Your Heart (1988)
> Prior Top 40 hit: Keep Me Cryin’ (1976)
> Career Top 40 hits: 14 songs (135 weeks total)
55. Gladys Knight And The Pips
> Gap between Top 40 hits: 12 years, 1 month
> Comeback song: Love Overboard (1988)
> Prior Top 40 hit: Part Time Love (1975)
> Career Top 40 hits: 25 songs (214 weeks total)
[in-text-ad]
54. Enya
> Gap between Top 40 hits: 12 years, 4 months
> Comeback song: Only Time (2001)
> Prior Top 40 hit: Orinoco Flow (Sail Away) (1989)
> Career Top 40 hits: 3 songs (55 weeks total)
53. Dave Edmunds
> Gap between Top 40 hits: 12 years, 5 months
> Comeback song: Slipping Away (1983)
> Prior Top 40 hit: I Hear You Knocking (1971)
> Career Top 40 hits: 2 songs (10 weeks total)
52. Cliff Richard
> Gap between Top 40 hits: 12 years, 6 months
> Comeback song: Devil Woman (1976)
> Prior Top 40 hit: It’s All In The Game (1964)
> Career Top 40 hits: 9 songs (83 weeks total)
24/7 Wall St.
51. Gwen Stefani
> Gap between Top 40 hits: 12 years, 7 months
> Comeback song: Nobody But You (w/ Blake Shelton) (2020)
> Prior Top 40 hit: The Sweet Escape (w/ Akon) (2007)
> Career Top 40 hits: 10 songs (184 weeks total)
50. Conway Twitty
> Gap between Top 40 hits: 12 years, 7 months
> Comeback song: You’ve Never Been This Far Before (1973)
> Prior Top 40 hit: C’est Si Bon (It’s So Good) (1961)
> Career Top 40 hits: 9 songs (72 weeks total)
49. Rakim
> Gap between Top 40 hits: 12 years, 8 months
> Comeback song: Addictive (w/ Truth Hurts) (2002)
> Prior Top 40 hit: Friends (w/ Jody Watley & Eric. B) (1989)
> Career Top 40 hits: 2 songs (27 weeks total)
[in-text-ad-2]
48. Donny Osmond
> Gap between Top 40 hits: 12 years, 8 months
> Comeback song: Soldier Of Love (1989)
> Prior Top 40 hit: C’mon Marianne (1976)
> Career Top 40 hits: 12 songs (105 weeks total)
47. Jimmy Ruffin
> Gap between Top 40 hits: 12 years, 11 months
> Comeback song: Hold On To My Love (1980)
> Prior Top 40 hit: Gonna Give Her All The Love I’ve Got (1967)
> Career Top 40 hits: 4 songs (34 weeks total)
46. Kylie Minogue
> Gap between Top 40 hits: 13 years
> Comeback song: Can’t Get You Out Of My Head (2002)
> Prior Top 40 hit: It’s No Secret (1989)
> Career Top 40 hits: 5 songs (38 weeks total)
45. INXS
> Gap between Top 40 hits: 13 years
> Comeback song: Pretty Vegas (2005)
> Prior Top 40 hit: Not Enough Time (1992)
> Career Top 40 hits: 10 songs (100 weeks total)
[in-text-ad]
44. Sonny Charles And The Checkmates
> Gap between Top 40 hits: 13 years, 6 months
> Comeback song: Put It In A Magazine (1983)
> Prior Top 40 hit: Black Pearl (1969)
> Career Top 40 hits: 2 songs (12 weeks total)
43. Jimmy Dean
> Gap between Top 40 hits: 13 years, 7 months
> Comeback song: I.O.U. (1976)
> Prior Top 40 hit: Little Black Book (1962)
> Career Top 40 hits: 7 songs (42 weeks total)
42. The Beatles
> Gap between Top 40 hits: 13 years, 7 months
> Comeback song: Free As A Bird (1995)
> Prior Top 40 hit: Got To Get You Into My Life (1976)
> Career Top 40 hits: 50 songs (430 weeks total)
24/7 Wall St.
41. Eagles
> Gap between Top 40 hits: 13 years, 9 months
> Comeback song: Get Over It (1994)
> Prior Top 40 hit: Seven Bridges Road (1981)
> Career Top 40 hits: 17 songs (168 weeks total)
40. Murray Head
> Gap between Top 40 hits: 13 years, 9 months
> Comeback song: One Night In Bangkok (1985)
> Prior Top 40 hit: Superstar (w/ the Trinidad Singers) (1971)
> Career Top 40 hits: 2 songs (21 weeks total)
39. Sergio Mendes
> Gap between Top 40 hits: 14 years, 4 months
> Comeback song: Never Gonna Let You Go (1983)
> Prior Top 40 hit: Scarborough Fair (1968)
> Career Top 40 hits: 5 songs (50 weeks total)
[in-text-ad-2]
38. Weird Al Yankovic
> Gap between Top 40 hits: 14 years, 5 months
> Comeback song: White & Nerdy (2006)
> Prior Top 40 hit: Smells Like Nirvana (1992)
> Career Top 40 hits: 4 songs (20 weeks total)
37. Radiohead
> Gap between Top 40 hits: 14 years, 7 months
> Comeback song: Nudе (2008)
> Prior Top 40 hit: Creep (1993)
> Career Top 40 hits: 2 songs (6 weeks total)
36. Meat Loaf
> Gap between Top 40 hits: 14 years, 9 months
> Comeback song: I’d Do Anything For Love (But I Won’t Do That) (1993)
> Prior Top 40 hit: You Took The Words Right Out Of My Mouth (1979)
> Career Top 40 hits: 7 songs (61 weeks total)
35. Carly Simon
> Gap between Top 40 hits: 14 years, 10 months
> Comeback song: Son Of A Gun (w/ Janet, Missy Elliott, & P. Diddy) (2001)
> Prior Top 40 hit: Coming Around Again (1986)
> Career Top 40 hits: 13 songs (123 weeks total)
[in-text-ad]
34. Billy Ray Cyrus
> Gap between Top 40 hits: 15 years, 4 months
> Comeback song: Ready, Set, Don’t Go (w/ Miley Cyrus) (2008)
> Prior Top 40 hit: Achy Breaky Heart (1992)
> Career Top 40 hits: 3 songs (67 weeks total)
33. Kenny Rogers
> Gap between Top 40 hits: 15 years, 5 months
> Comeback song: Buy Me A Rose (w/ Alison Krauss & Billy Dean) (2000)
> Prior Top 40 hit: What About Me? (w/ Kim Carnes & James Ingram) (1984)
> Career Top 40 hits: 25 songs (246 weeks total)
32. Alabama
> Gap between Top 40 hits: 16 years
> Comeback song: God Must Have Spent A Little More Time On You (w/ ‘N Sync) (1999)
> Prior Top 40 hit: The Closer You Get (1983)
> Career Top 40 hits: 6 songs (43 weeks total)
31. Guns N’ Roses
> Gap between Top 40 hits: 16 years, 1 month
> Comeback song: Chinese Democracy (2008)
> Prior Top 40 hit: November Rain (1992)
> Career Top 40 hits: 9 songs (97 weeks total)
30. Barry White
> Gap between Top 40 hits: 16 years, 5 months
> Comeback song: Practice What You Preach (1994)
> Prior Top 40 hit: Oh What A Night For Dancing (1978)
> Career Top 40 hits: 11 songs (99 weeks total)
29. Clipse
> Gap between Top 40 hits: 16 years, 10 months
> Comeback song: Use This Gospel (w/ Kanye West & Kenny G) (2019)
> Prior Top 40 hit: When The Last Time (2002)
> Career Top 40 hits: 3 songs (21 weeks total)
[in-text-ad-2]
28. Santana
> Gap between Top 40 hits: 16 years, 10 months
> Comeback song: Smooth (w/ Rob Thomas) (1999)
> Prior Top 40 hit: Hold On (1982)
> Career Top 40 hits: 15 songs (228 weeks total)
27. Del Shannon
> Gap between Top 40 hits: 16 years, 10 months
> Comeback song: Sea Of Love (1982)
> Prior Top 40 hit: Stranger In Town (1965)
> Career Top 40 hits: 9 songs (62 weeks total)
26. David Cassidy
> Gap between Top 40 hits: 17 years, 9 months
> Comeback song: Lyin’ To Myself (1990)
> Prior Top 40 hit: Looking Through The Eyes Of Love (w/ The Partridge Family) (1973)
> Career Top 40 hits: 12 songs (82 weeks total)
25. New Kids On The Block
> Gap between Top 40 hits: 17 years, 10 months
> Comeback song: Summertime (2008)
> Prior Top 40 hit: Tonight (1990)
> Career Top 40 hits: 10 songs (103 weeks total)
[in-text-ad]
24. Dusty Springfield
> Gap between Top 40 hits: 17 years, 11 months
> Comeback song: What Have I Done To Deserve This? (w/ Pet Shop Boys) (1987)
> Prior Top 40 hit: A Brand New Me (1969)
> Career Top 40 hits: 11 songs (77 weeks total)
23. Nas
> Gap between Top 40 hits: 18 years
> Comeback song: Sorry Not Sorry (w/ DJ Khaled, Jay-Z, & James Fauntleroy) (2021)
> Prior Top 40 hit: I Can (2003)
> Career Top 40 hits: 8 songs (86 weeks total)
22. The Monkees
> Gap between Top 40 hits: 18 years
> Comeback song: That Was Then, This Is Now (1986)
> Prior Top 40 hit: D. W. Washburn (1968)
> Career Top 40 hits: 12 songs (91 weeks total)
21. Ray Charles
> Gap between Top 40 hits: 18 years, 7 months
> Comeback song: I’ll Be Good To You (w/ Quincy Jones & Chaka Khan) (1989)
> Prior Top 40 hit: Don’t Change On Me (1971)
> Career Top 40 hits: 31 songs (191 weeks total)
20. Billy Vera
> Gap between Top 40 hits: 18 years, 9 months
> Comeback song: At This Moment (1986)
> Prior Top 40 hit: Country Girl – City Man (w/ Judy Clay) (1968)
> Career Top 40 hits: 2 songs (16 weeks total)
19. Gary U.S. Bonds
> Gap between Top 40 hits: 18 years, 9 months
> Comeback song: This Little Girl (1981)
> Prior Top 40 hit: Seven Day Weekend (1962)
> Career Top 40 hits: 7 songs (57 weeks total)
[in-text-ad-2]
18. Johnny Mathis
> Gap between Top 40 hits: 18 years, 11 months
> Comeback song: Friends In Love (w/ Dionne Warwick) (1982)
> Prior Top 40 hit: Every Step Of The Way (1963)
> Career Top 40 hits: 10 songs (67 weeks total)
17. Willie Nelson
> Gap between Top 40 hits: 19 years
> Comeback song: Beer For My Horses (w/ Toby Keith) (2003)
> Prior Top 40 hit: To All The Girls I’ve Loved Before (w/ Julio Iglesias) (1984)
> Career Top 40 hits: 6 songs (61 weeks total)
16. Kenny G
> Gap between Top 40 hits: 19 years, 10 months
> Comeback song: Use This Gospel (w/ Kanye West and Clipse) (2019)
> Prior Top 40 hit: Auld Lang Syne (2000)
> Career Top 40 hits: 6 songs (45 weeks total)
15. Patti LaBelle
> Gap between Top 40 hits: 21 years, 2 months
> Comeback song: New Attitude (1985)
> Prior Top 40 hit: You’ll Never Walk Alone (w/ The Blue Belles) (1964)
> Career Top 40 hits: 5 songs (31 weeks total)
[in-text-ad]
14. The Isley Brothers
> Gap between Top 40 hits: 21 years, 2 months
> Comeback song: Contagious (2001)
> Prior Top 40 hit: Don’t Say Goodnight (It’s Time For Love) (Parts 1 & 2) (1980)
> Career Top 40 hits: 12 songs (105 weeks total)
13. Dolly Parton
> Gap between Top 40 hits: 22 years, 2 months
> Comeback song: When I Get Where I’m Going (w/ Brad Paisley) (2006)
> Prior Top 40 hit: Islands In The Stream (w/ Kenny Rogers) (1983)
> Career Top 40 hits: 8 songs (74 weeks total)
12. Aaron Neville
> Gap between Top 40 hits: 22 years, 8 months
> Comeback song: Don’t Know Much (w/ Linda Ronstadt) (1989)
> Prior Top 40 hit: Tell It Like It Is (1966)
> Career Top 40 hits: 4 songs (48 weeks total)
24/7 Wall St.
11. Roy Orbison
> Gap between Top 40 hits: 22 years, 9 months
> Comeback song: You Got It (1989)
> Prior Top 40 hit: Twinkle Toes (1966)
> Career Top 40 hits: 23 songs (172 weeks total)
10. Tammy Wynette
> Gap between Top 40 hits: 23 years
> Comeback song: Justified And Ancient (w/ The KLF) (1992)
> Prior Top 40 hit: Stand By Your Man (1968)
> Career Top 40 hits: 2 songs (21 weeks total)
9. Jimmy Buffett
> Gap between Top 40 hits: 23 years, 9 months
> Comeback song: It’s Five O’Clock Somewhere (w/ Alan Jackson) (2003)
> Prior Top 40 hit: Fins (1979)
> Career Top 40 hits: 7 songs (59 weeks total)
[in-text-ad-2]
8. Jimmy Cliff
> Gap between Top 40 hits: 23 years, 10 months
> Comeback song: I Can See Clearly Now (1993)
> Prior Top 40 hit: Wonderful World, Beautiful People (1969)
> Career Top 40 hits: 2 songs (21 weeks total)
7. Charlie Sexton
> Gap between Top 40 hits: 23 years, 10 months
> Comeback song: Hallelujah (w/ Justin Timberlake & Matt Morris) (2010)
> Prior Top 40 hit: Beat’s So Lonely (1986)
> Career Top 40 hits: 2 songs (11 weeks total)
6. Mick Jagger
> Gap between Top 40 hits: 24 years, 2 months
> Comeback song: T.H.E (The Hardest Ever) (w/ will.i.am & Jennifer Lopez) (2011)
> Prior Top 40 hit: Let’s Work (1987)
> Career Top 40 hits: 5 songs (24 weeks total)
5. Dobie Gray
> Gap between Top 40 hits: 24 years, 3 months
> Comeback song: Drift Away (w/ Uncle Kracker) (2003)
> Prior Top 40 hit: You Can Do It (1979)
> Career Top 40 hits: 4 songs (52 weeks total)
[in-text-ad]
4. Paul McCartney
> Gap between Top 40 hits: 25 years, 6 months
> Comeback song: Only One (w/ Kanye West) (2015)
> Prior Top 40 hit: My Brave Face (1989)
> Career Top 40 hits: 20 songs (205 weeks total)
3. Snow
> Gap between Top 40 hits: 25 years, 9 months
> Comeback song: Con Calma (w/ Daddy Yankee & Katy Perry) (2019)
> Prior Top 40 hit: Girl, I’ve Been Hurt (1993)
> Career Top 40 hits: 3 songs (38 weeks total)
2. Ozzy Osbourne
> Gap between Top 40 hits: 27 years, 5 months
> Comeback song: Take What You Want (w/ Post Malone & Travis Scott) (2019)
> Prior Top 40 hit: Mama, I’m Coming Home (1992)
> Career Top 40 hits: 3 songs (23 weeks total)
[in-text-ad-2]
1. David Bowie
> Gap between Top 40 hits: 28 years, 4 months
> Comeback song: Lazarus (2016)
> Prior Top 40 hit: Never Let Me Down (1987)
> Career Top 40 hits: 13 songs (118 weeks total)
Find a Qualified Financial Advisor (Sponsor)
Finding a qualified financial advisor doesn’t have to be hard. SmartAsset’s free tool matches you with up to 3 fiduciary financial advisors in your area in 5 minutes. Each advisor has been vetted by SmartAsset and is held to a fiduciary standard to act in your best interests. If you’re ready to be matched with local advisors that can help you achieve your financial goals, get started now.
Thank you for reading! Have some feedback for us?
Contact the 24/7 Wall St. editorial team.
Latest from 24/7
