What follows is a list of 125 household-name artists grouped by the last years in which they appeared on a single that hit the Top 40 of Billboard's Hot 100 chart in America.
I included mostly living artists, since the idea is that they could still have another hit some day. (In cases where the artists have died since I compiled this list, I put them in parentheses. Let me know who's missing!)
As a recovering teen chart nut, I find this stuff fascinating. It speaks to their relevance as artists in some cases, but speaks to the relevance of having a "hit single" in cases where the artists are clearly still quite successful by other measures.
Most of all, it's just wow-inducing to see how long it's been for some of these artists, who have sold millions and millions of records in their storied careers.
It's also interesting seeing the groups of artists who enjoyed their last Top 40 success together ... Gloria Gaynor and Patti Smith, for example, both hit the Top 40 for the last time in the very same year.
(Please feel free to correct me if I am wrong on any; it's hard juggling artists' singles, featured appearances, etc.)
Never in the Top 40
Andrea Bocelli
Debbie Harry (as solo artist)
Courtney Love (solo or with Hole)
Marilyn Manson
Liza Minnelli
Last Top 40 Hit: 1964
Connie Francis
Last Top 40 Hit: 1967
Lesley Gore
Last Top 40 Hit: 1971
Van Morrison
Last Top 40 Hit: 1977
Lynyrd Skynyrd
Last Top 40 Hit: 1978
Gloria Gaynor
Patti Smith
Last Top 40 Hit: 1979
Bob Dylan
Pink Floyd
Last Top 40 Hit: 1980
Carole King
Wayne Newton
Neil Sedaka
Last Top 40 Hit: 1981
James Taylor
Last Top 40 Hit: 1982
Blondie
Neil Diamond
Rush
Last Top 40 Hit: 1983
Paul Anka
Barry Manilow
Last Top 40 Hit: 1984
The Go-Go's
Julio Iglesias
Diana Ross
Last Top 40 Hit: 1985
Kate Bush
Dire Straits
Willie Nelson
Olivia Newton-John
Last Top 40 Hit: 1986
Jackson Browne
The Pointer Sisters
Paul Simon
The Talking Heads
Last Top 40 Hit: 1987
(Note: Bowie's last year for a Top 40 hit prior to his death; "Lazarus" hit #40 the week after he died in 2016)
Dionne Warwick
Stevie Wonder
Last Top 40 Hit: 1988
Foreigner
(Note: Glenn Frey's last hit before his 2016 death.)
Al Green
Joni Mitchell
Pet Shop Boys
Robert Plant
Last Top 40 Hit: 1989
The Bangles
Pat Benatar
Elvis Costello
Cyndi Lauper
Stevie Nicks
The Rolling Stones
Last Top 40 Hit: 1990
Belinda Carlisle
Fleetwood Mac
Hall & Oates
Kiss
Bette Midler
Last Top 40 Hit: 1991
Roberta Flack
Huey Lewis & the News
Last Top 40 Hit: 1992
The Cure
Boy George
Peter Gabriel
Don Henley
k.d. lang
Ozzy Osbourne
Sade
Last Top 40 Hit: 1993
Duran Duran
Billy Joel
New Order
Tina Turner
Last Top 40 Hit: 1994
Beck
R.E.M.
(Note: Tom Petty's last Top 40 before he died in 2017.)
Last Top 40 Hit: 1995
Annie Lennox
Meat Loaf
Van Halen
Neil Young*
*Young played on a Pearl Jam hit in 1995, but received no chart credit. Prior to this, his most recent Top 40 hit was in 1972.
Last Top 40 Hit: 1996
Bryan Adams
(Note: George Michael's last hit before his death in 2016)
Journey
Lionel Richie
Last Top 40 Hit: 1997
Depeche Mode
Bruce Springsteen
Last Top 40 Hit: 1998
Cher
Aretha Franklin
Oasis
(Note: Prince's last hit before his 2016 death)
Spice Girls
Rod Stewart
Last Top 40 Hit: 1999
Garth Brooks
Phil Collins
Gloria Estefan
Kenny G
Garbage
Ice Cube
Elton John
Kenny Rogers
Last Top 40 Hit: 2000
Eric Clapton
Last Top 40 Hit: 2001
Aerosmith
Enya
Ricky Martin
Last Top 40 Hit: 2002
Céline Dion
Alanis Morisette
*NSYNC
Last Top 40 Hit: 2003
Jewel
Shania Twain
Last Top 40 Hit: 2005
Backstreet Boys
Nine Inch Nails
Dolly Parton
U2
Last Top 40 Hit: 2007
Bon Jovi
Santana
Last Top 40 Hit: 2008
Sheryl Crow
Guns 'N Roses
Metallica
New Kids on the Block
Last Top 40 Hit: 2009
Green Day
Dave Matthews Band
Last Top 40 Hit: 2010
Janet Jackson* (2008)
LL Cool J* (2006)
Barbra Streisand* (1996)
*Only charted due to "We Are the World 25 for Haiti." See parenthetics for previous year with a hit.
Last Top 40 Hit: 2011
Mick Jagger
The Red Hot Chili Peppers
Shakira
Last Top 40 Hit: 2012
Eminem
Madonna
Last Top 40 Hit: 2013
Mariah Carey
Last Top 40 Hit: 2014
Jennifer Lopez
Last Top 40 Hit: 2015
Paul McCartney
Full Details (Roughly Chronological)
Andrea Bocelli = never
Debbie Harry = never
Courtney Love = never
Marilyn Manson = never
Liza Minnelli = never
Connie Francis, "Be Anything (But Be Mine)," #25 (1964)
Lesley Gore, "California Nights," #16 (1967)
Van Morrison, "Wild Night," #28 (1971)
Lynyrd Skynyrd, "What's Your Name?" #13 (1977)
Patti Smith, "Because the Night," #13 (1978)
Gloria Gaynor, "I Will Survive," #1 (1978)
Pink Floyd, "Another Brick in the Wall (Part II)," #1 (1979)
Bob Dylan, "Gotta Serve Somebody," #24 (1979)
Carole King, "One Fine Day,"#12 (1980)
Wayne Newton, "Years," #35 (1980)
Neil Sedaka, "Should've Never Let You Go" (duet with Dara Sedaka), #19 (1980)
James Taylor, "Her Town Too" (duet with J.D. Souther), #11 (1981)
Blondie, "Island of Lost Souls," #37 (1982)
ABBA, "When All is Said and Done," #27 (1982)
Neil Diamond, "Heartlight," #5 (1982)
Rush, "New World Man," #21 (1982)
Paul Anka, "Hold Me 'Til the Morning Comes," #40 (1983)
Barry Manilow, "Read 'Em and Weep," #18 (1983)
Julio Iglesias, "To All the Girls I've Loved Before" (duet with Willie Nelson), #5 (1984)
Diana Ross, "Missing You," #10 (1984)
The Go-Go's, "Turn to You," #32 (1984)
Willie Nelson, "We Are the World" (Various), #1 (1985)
Olivia Newton-John, "Soul Kiss," #20 (1985)
Dire Straits, "Walk of Life," #7 (1985)
Kate Bush, "Running Up That Hill," #30 (1985)
Paul Simon, "You Can Call Me Al," #23 (1986)
The Talking Heads, "Wild Wild Life," #25 (1986)
Jackson Browne, "For America," #30 (1986)
The Pointer Sisters, "Goldmine," #33 (1986)
Dionne Warwick, "Love Power" (duet with Jeffrey Osborne), #12 (1987)
David Bowie, "Never Let Me Down," #27 (1987)
Stevie Wonder, "Skeletons," #19 (1987)
Pet Shop Boys, "Domino Dancing," #18 (1988)
Robert Plant, "Tall Cool One," #25 (1988)
Foreigner, "I Don't Wanna Live Without You," #5 (1988)
Al Green, "Put a Little Love in Your Heart" (duet with Annie Lennox), #9 (1988)
Joni Mitchell, "Snakes and Ladders," #32 (1988)
Glenn Frey, "True Love," #13 (1988)
Pat Benatar, "All Fired Up," #18 (1989)
The Bangles, "Be With You," #30 (1989)
The Rolling Stones, "Rock and a Hard Place," #23 (1989)
Cyndi Lauper, "I Drove All Night," #6 (1989)
Stevie Nicks, "Rooms on Fire," #16 (1989)
Paul McCartney, "My Brave Face," #25 (1989)
Elvis Costello, "Veronica," #19 (1989)
Kiss, "Forever (Remix)," #8 (1990)
Bette Midler, "From a Distance," #2 (1990)
Belinda Carlisle, "Summer Rain," #30 (1990)
Fleetwood Mac, "Save Me," #33 (1990)
Hall & Oates, "So Close," #11 (1990)
Huey Lewis & the News, "It Hit Me Like a Hammer," #21 (1991)
Roberta Flack, "Set the Night to Music" (duet with Maxi Priest), #6 (1991)
Peter Gabriel, "Steam," #32 (1992)
Sade, "No Ordinary Love," #20 (1992)
Boy George, "The Crying Game," #15 (1992)
The Cure, "Friday I'm in Love," #18 (1992)
k.d. lang, "Constant Craving," #38 (1992)
Don Henley, "Sometimes Love Just Ain't Enough" (duet with Patty Smyth), #2 (1992)
Ozzy Osbourne, "Mama, I'm Coming Come," #28 (1992)
Duran Duran, "Come Undone" #7 (1993)
New Order, "Regret," #28 (1993)
Tina Turner, "I Don't Wanna Fight," #9 (1993)
Billy Joel, "All About Soul," #29 (1993)
R.E.M., "Bang and Blame," #19 (1994)
Tom Petty, "You Don't Know How It Feels," #13 (1994)
Beck, "Loser," #10 (1994)
Meat Loaf, "I'd Lie for You (and That's the Truth)" (with Patti Russo), #13 (1995)
Neil Young, "I Got Id" by Pearl Jam, #7 (1995) [Young played guitar on the track, but received no Billboard credit; previous entry was "Old Man," #31 (1972)]
Annie Lennox, "No More I Love Yous," #23 (1995)
Van Halen, "Can't Stop Lovin' You," #30 (1995)
George Michael, "Fastlove," #8 (1996)
Journey, "When You Love a Woman," #12 (1996)
Lionel Richie, "Don't Wanna Lose You," #39 (1996)
Bryan Adams, "I Finally Found Someone" (duet with Barbra Streisand), #8 (1996)
Depeche Mode, "It's No Good," #38 (1997)
Bruce Springsteen, "Secret Garden," #19 (1997)
Cher, "Believe," #1 (1998)
Rod Stewart, "Ooh La La," #39 (1998)
Aretha Franklin, "A Rose is Still a Rose," #26 (1998)
Prince, "1999," #40 (1998) [non-rerelease = "I Hate U," #12 (1995)]
Spice Girls, "Goodbye," #11 (1998)
Oasis, "Don't Go Away," #35 (1998)
Kenny G, "Auld Lang Syne," #7 (1999)
Elton John, "Written in the Stars" (duet with LeAnn Rimes), #29 (1999)
Phil Collins, "You'll Be in My Heart," #21 (1999)
Gloria Estefan, "Music of My Heart" (duet with *NSYNC), #2 (1999)
Garth Brooks, "Lost in You" (as "Chris Gaines"), #5 (1999)
Ice Cube, "You Can Do It" (with Mack 10 & Ms. Toi), #35 (1999)
Garbage, "When I Grow Up," #4 (1999)
Kenny Rogers, "Buy Me a Rose" (with Alison Krauss & Billy Dean), #40 (1999)
Eric Clapton, "Riding with the King" (duet with B.B. King), #26 (2000)
Ricky Martin, "Nobody Wants to Be Lonely" (duet with Christina Aguilera), #13 (2001)
Aerosmith, "Jaded," #7 (2001)
Enya, "Only Time," #10 (2001)
Celine Dion, "A New Day Has Come," #22 (2002)
Alanis Morisette, "Hands Clean," #23 (2002)
*NSYNC, "Girlfriend" (feat. Nelly), #5 (2002)
Shania Twain, "Forever and for Always," #20 (2003)
Jewel, "Intuition," #20 (2003)
Dolly Parton, "When I Get Where I'm Going" (duet with Brad Paisley), #39 (2005)
U2, "Original of the Species," #23 (2005)
Backstreet Boys, "Incomplete," #13 (2005)
Nine Inche Nails, "The Hand That Feeds," #31 (2005)
Bon Jovi, "(You Want To) Make a Memory," #27 (2007)
Santana, "Into the Night" (feat. Chad Kroeger), #26 (2007)
Metallica, "The Day That Never Comes," #31 (2008)
Guns N' Roses, "Chinese Democracy," #34 (2008)
Sheryl Crow, "Just Stand Up!" (Various), #11 (2008)
New Kids on the Block, "Summertime" (feat. Ne-Yo), #35 (2008)
Green Day, "21 Guns," #22 (2009)
Dave Matthews Band, "Funny the Way It Is," #37 (2009)
Barbra Streisand, "We Are the World 25 for Haiti" (Various), #2 (2010) [non-group = "I Finally Found Someone" (duet with Bryan Adams), #8 (1996)]
Janet Jackson, "We Are the World 25 for Haiti" (Various), #2 (2010) [non-group = "Feedback," #19 (2008)]
LL Cool J, "We Are the World 25 for Haiti" (Various), #2 (2010) [non-group = "Control Myself" (feat. Jennifer Lopez), #4 (2006)]
The Red Hot Chili Peppers, "The Adventures of Rain Dance Maggie," #38 (2011)
Shakira, "Loca" (feat. El Cata & Dizzee Rascal), #32 (2011)
Mick Jagger, "T.H.E. (The Hardest Ever" (will.i.am feat. Mick Jagger & Jennifer Lopez), #36 (2011)
Eminem, "My Life" (with 50 Cent & Adam Levine), #27 (2012)
Madonna, "Give Me All Your Luvin'," #10 (2012)
Mariah Carey, "Beautiful," #15 (2013)
Jennifer Lopez, "Booty," #18 (2014)
Paul McCartney, "FourFiveSeconds" (Kanye West, Rihanna & Paul McCartney), #4 (2015)
I think you forgot to include Paul McCartney’s hit with Kanye West and Rihanna on FourFiveSeconds, although I don’t think he sang on this record.