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The Longest Careers on the Year-End Chart

Staying relevant for decades is the hardest trick in pop. These artists placed songs on the year-end chart across the longest spans of time, measured from their first year-end hit to their most recent.

Brenda Lee tops the list: the first and latest year-end hits are 65 years apart. Long spans often come from comebacks, reissues, holiday songs or a guest spot on a younger star's record.

#	Artist	First	Latest	Span	Entries
1	Brenda Lee	1960	2025	65 years	16
2	Burl Ives	1962	2024	62 years	5
3	Elton John	1972	2022	50 years	28
4	Michael Jackson	1972	2014	42 years	26
5	Wham!	1985	2025	40 years	8
6	The Isley Brothers	1962	2001	39 years	4
7	Marvin Gaye	1963	2001	38 years	13
8	Santana	1970	2008	38 years	9
9	Mariah Carey	1990	2025	35 years	39
10	Cher	1965	1999	34 years	16
11	Jimmy Buffett	1977	2011	34 years	3
12	The Four Seasons	1962	1994	32 years	8
13	Aretha Franklin	1967	1998	31 years	15
14	Usher	1997	2024	27 years	31
15	Lil Wayne	1999	2025	26 years	36
16	The Beach Boys	1962	1988	26 years	13
17	Aerosmith	1976	2001	25 years	12
18	Madonna	1984	2008	24 years	36
19	Eminem	2000	2024	24 years	24
20	Dusty Springfield	1964	1988	24 years	3
21	Aaron Neville	1967	1991	24 years	3
22	Rod Stewart	1971	1994	23 years	15
23	Barbra Streisand	1974	1997	23 years	9
24	Eric Clapton	1974	1997	23 years	8
25	Blake Shelton	2001	2024	23 years	8

Hear any of these. Tap ▶ next to a song to play it on the Hey DJ 4U decks: a 30-second preview, or the full song with Apple Music.

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Based on the year-end Top 100 singles charts, 1956–2025, as compiled on Wikipedia. Artist counts include lead and featured credits. How we handle the data.