The 25 recording artists who show up again and again on the Billboard Hot 100 all have appeared on the hallowed singles chart in at least 22 different years. Four of them have had songs on the Hot 100 for 30 different years. (These are the artists with the longest streaks on the Billboard Hot 100.)
To determine the artists who keep coming back to the Billboard Hot 100, 24/7 Tempo reviewed data on Billboard Hot 100 chart performance. Artists were ranked based on the number of different years, not necessarily consecutively, that they appeared on the Hot 100 – a measure of career longevity. Any years in which artists appeared on the Hot 100 as either a lead or featured artist were counted toward their total years. Madonna, for example, had entries on the Hot 100 every year from 1983 to 2006, then again in 2008 and 2009, 2012, 2015, and again in 2023, summing to a total of 29 different years on the charts. Chart data is current through Sept. 9, 2023. (Billboard sources its data from Luminate, a company collecting data on music and other entertainment forms.)
Our list is a veritable who’s who of the greatest performers in the popular-music era, some of them dating to the 1950s. Among them are Madonna, Michael Jackson, the Rolling Stones, Barbra Streisand, Paul McCartney, Mariah Carey, and Elvis Presley. Elvis Presley and Jay-Z had the most number of singles on the list, each with more than 100. The average number of songs charted by the performers on this list is 59.
The artists on our list who appeared earliest on the Hot 100 were Presley, Andy Williams, and James Brown, all of whom debuted in 1958. The holiday offerings from Presley (“Blue Christmas”) and Williams (“It’s the Most Wonderful Time of the Year”) each appeared on the Hot 100 in January of this year. Eleven artists had songs that last entered the chart in 2023. Included among them is the artist with the longest tenure of any performer on our list, who first charted on the Billboard Hot 100 in 1970 – Elton John. (These are Elton John’s biggest hits according to Billboard.)
25. Brenda Lee
> No. of different years on the Hot 100: 22
> First appearance: “Sweet Nothin’s” (Dec. 21, 1959)
> Most recent appearance: “Rockin’ Around the Christmas Tree” (Jan. 7, 2023)
> Total career Hot 100 appearances: 48
24. Keith Urban
> No. of different years on the Hot 100: 22
> First appearance: “Your Everything” (July 15, 2000)
> Most recent appearance: “Wild Hearts” (June 11, 2022)
> Total career Hot 100 appearances: 46
23. James Brown
> No. of different years on the Hot 100: 22
> First appearance: “Try Me” (ft. the Famous Flames) (Dec. 15, 1958)
> Most recent appearance: “Gravity” (Oct. 25, 1986)
> Total career Hot 100 appearances: 88
22. Chicago
> No. of different years on the Hot 100: 22
> First appearance: “Questions 67 and 68” (Aug. 9, 1969)
> Most recent appearance: “Chasin’ the Wind” (April 6, 1991)
> Total career Hot 100 appearances: 46
21. Whitney Houston
> No. of different years on the Hot 100: 22
> First appearance: “Hold Me” (ft. Teddy Pendergrass) (June 9, 1984)
> Most recent appearance: “Higher Love” (ft. Kygo) (Nov. 16, 2019)
> Total career Hot 100 appearances: 40
20. Paul McCartney
> No. of different years on the Hot 100: 23
> First appearance: “Another Day/Oh Woman Oh Why” (March 6, 1971)
> Most recent appearance: “Wonderful Christmastime” (Jan. 7, 2023)
> Total career Hot 100 appearances: 47
19. Andy Williams
> No. of different years on the Hot 100: 23
> First appearance: “Promise Me, Love” (Sept. 1, 1958)
> Most recent appearance: “It’s the Most Wonderful Time of the Year” (Jan. 7, 2023)
> Total career Hot 100 appearances: 41
18. Eminem
> No. of different years on the Hot 100: 23
> First appearance: “My Name Is” (Feb. 27, 1999)
> Most recent appearance: “Use This Gospel (Remix)” (ft. DJ Khaled & Kanye West) (Sept. 10, 2022)
> Total career Hot 100 appearances: 95
17. Prince
> No. of different years on the Hot 100: 23
> First appearance: “Soft and Wet” (Nov. 4, 1978)
> Most recent appearance: “Purple Rain” (May 14, 2016)
> Total career Hot 100 appearances: 47
16. U2
> No. of different years on the Hot 100: 24
> First appearance: “New Year’s Day” (April 2, 1983)
> Most recent appearance: “XXX.” (ft. Kendrick Lamar) (May 20, 2017)
> Total career Hot 100 appearances: 34
15. Barbra Streisand
> No. of different years on the Hot 100: 24
> First appearance: “People” (April 4, 1964)
> Most recent appearance: “I Finally Found Someone” (ft. Bryan Adams) (April 5, 1997)
> Total career Hot 100 appearances: 41
14. Jay-Z
> No. of different years on the Hot 100: 24
> First appearance: “Dead Presidents” (ft. Foxxy Brown) (April 6, 1996)
> Most recent appearance: “Umbrella” (ft. Rihanna) (Feb. 25, 2023)
> Total career Hot 100 appearances: 105
13. Usher
> No. of different years on the Hot 100: 24
> First appearance: “Can U Get Wit It” (Sept. 3, 1994)
> Most recent appearance: “Good Good” (ft. Summer Walker & 21 Savage) (Sept. 9, 2023)
> Total career Hot 100 appearances: 53
12. Kenny Chesney
> No. of different years on the Hot 100: 25
> First appearance: “That’s Why I’m Here” (May 9, 1998)
> Most recent appearance: “Half of My Hometown” (ft. Kelsea Ballerini) (April 9, 2022)
> Total career Hot 100 appearances: 58
11. Aretha Franklin
> No. of different years on the Hot 100: 26
> First appearance: “Won’t Be Long” (ft. the Ray Bryant Combo) (Feb. 27, 1961)
> Most recent appearance: “Here We Go Again” (Sept. 26, 1998)
> Total career Hot 100 appearances: 73
10. The Beach Boys
> No. of different years on the Hot 100: 27
> First appearance: “Surfin” (Feb. 17, 1962)
> Most recent appearance: “Little Saint Nick” (Jan. 7, 2023)
> Total career Hot 100 appearances: 55
9. The Rolling Stones
> No. of different years on the Hot 100: 27
> First appearance: “Not Fade Away” (May 2, 1964)
> Most recent appearance: “Sympathy for the Devil (Remixes)” (Oct. 4, 2003)
> Total career Hot 100 appearances: 57
8. Tim McGraw
> No. of different years on the Hot 100: 28
> First appearance: “Indian Outlaw” (March 5, 1994)
> Most recent appearance: “Standing Room Only” (Sept. 9, 2023)
> Total career Hot 100 appearances: 61
7. Stevie Wonder
> No. of different years on the Hot 100: 28
> First appearance: “Hey Harmonica Man” (June 13, 1964)
> Most recent appearance: “So What the Fuss” (April 9, 2005)
> Total career Hot 100 appearances: 63
6. Rod Stewart
> No. of different years on the Hot 100: 29
> First appearance: “Maggie May/Reason To Believe” (July 17, 1971)
> Most recent appearance: “Everyday” (ft. A$AP Rocky, Miguel, Mark Ronson) (June 27, 2015)
> Total career Hot 100 appearances: 52
5. Madonna
> No. of different years on the Hot 100: 29
> First appearance: “Holiday” (Oct. 29, 1983)
> Most recent appearance: “Popular” (ft. The Weeknd & Playboi Carti) (Sept. 9, 2023)
> Total career Hot 100 appearances: 58
4. Elvis Presley
> No. of different years on the Hot 100: 30
> First appearance: “Hard Headed Woman” (ft. the Jordanaires) (Aug. 11, 1958)
> Most recent appearance: “Blue Christmas” (Jan. 7, 2023)
> Total career Hot 100 appearances: 109
3. Michael Jackson
> No. of different years on the Hot 100: 33
> First appearance: “Got To Be There” (Oct. 30, 1971)
> Most recent appearance: “Thriller” (Nov. 12, 2022)
> Total career Hot 100 appearances: 50
2. Mariah Carey
> No. of different years on the Hot 100: 33
> First appearance: “Vision of Love” (June 2, 1990)
> Most recent appearance: “All I Want for Christmas Is You” (Jan. 7, 2023)
> Total career Hot 100 appearances: 49
1. Elton John
> No. of different years on the Hot 100: 34
> First appearance: “Border Song” (Aug. 15, 1970)
> Most recent appearance: “Hold Me Closer” (ft. Britney Spears) (Jan. 21, 2023)
> Total career Hot 100 appearances: 71