Magazine covers featuring musical artists are inherently cool, whether the reader is a tween or a boomer. They come loaded with style, after all. (How many different looks—including varieties-not-found-in-nature of hair color—have Madonna and Bowie rocked on their many covers over the decades?) The result: memorable, provocative and sometimes flat-out crazy images of the stars. But beyond the superficial, they also have chronicled the changes in the culture and the sounds of the times—consider Bob Dylan’s various transformations across 24(!) Rolling Stone covers. Not only have covers become part of music history and culture at large, but they also remain a potent tool for marketing artists. Musicians have a way of grabbing our attention—often, it’s while peering out from a newsstand shelf, be it Time, Playboy, Vanity Fair or GQ. Recent controversial covers include a naked Miley Cyrus on Rolling Stone and Pharrell Williams sporting a 10-gallon hat on Billboard. But the single most talked about of late is the current Vogue, featuring hip-hop star Kanye West and his reality-TV personality spouse Kim Kardashian (“Kimye”). Music covers have the power to provoke, to inspire—and to fascinate. There is no doubt they have given us some of the most iconic images in the history of pop culture. As an art director at a number of music publications over the years, I have seen fans obsess about who is on a cover and how they look. Readers have said to me: “You have to put [insert name of one-hit wonder] on the cover!” Or, “How could you put that no-talent [best-selling artist of the year] on your cover?” We hope this compilation will, likewise, encourage a vigorous exchange of opinions. 1 Eddie Cantor / Popular Songs / 1937 2 Marian Anderson / Time / 1946 3 Billie Holiday / Ebony / 1949 4 Dave Brubeck / Time / 1954 5 The Everly Brothers / Dig / 1958 6 Max Roach / Down Beat / 1958 7 Ricky Nelson / Life / 1958 8 Frank Sinatra / Hit Parade / 1958 9 Elvis Presley / Dig / 1958 10 Fabian / Dig / 1959 11 Little Richard / Hit Parade / 1959 12 Ray Charles / Jazz Magazine / 1961 13 Bob Dylan / Sing Out! / 1962 14 Thelonious Monk / Time / 1964 15 Frank Sinatra /Esquire / 1965 16 Barbra Streisand / Sunday New York News / 1965 17 Louis Armstrong / Life / 1966 18 Leontyne Price / Opera News / 1967 19 Bob Dylan / Oz / 1967 20 The Who / Cash Box / 1967 21 James Brown / Jet / 1968 22 John Lennon (The Beatles) / Look / 1968 23 John Lennon and Yoko Ono / Rolling Stone / 1968 24 Grace Slick (Jefferson Airplane) / Teenset / 1969 25 Miles Davis / Rolling Stone / 1969 26 Aretha Franklin / Ebony / 1971 27 James Taylor / Time / 1971 28 The Jackson 5 / Ebony / 1971 29 David Cassidy / Rolling Stone / 1972 30 Jerry Garcia / Rolling Stone / 1972 31 Isaac Hayes / Ebony / 1972 32 New York Dolls / Rock Scene / 1974 33 Sly Stone / Blues & Soul / 1974 34 Merle Haggard / Time / 1974 35 Bruce Springsteen / Time / 1975 36 Rolling Stones / Crawdaddy / 1975 37 Bob Marley / Rolling Stone / 1976 38 Lou Reed / Punk / 1976 39 Brian Wilson (Beach Boys) / Rolling Stone / 1976 40 Peter Frampton / People / 1977 41 Fleetwood Mac / Rolling Stone / 1977 42 Sex Pistols / Slash / 1977 43 Kiss / Marvel comic book / 1977 44 Patti Smith / Punk Rock / 1977 45 Dolly Parton / Playboy / 1978 46 Blues Brothers / Rolling Stone / 1979 47 Yoko Ono and John Lennon / Rolling Stone / 1981 48 Siouxsie Sioux (Siouxsie and the Banshees) / NME / 1982 49 Go-Go’s / Rolling Stone / 1982 50 Cher / Interview / 1982 51 Sade / i-D / 1983 52 Annie Lennox (Eurythmics) / The Face / 1983 53 New Order / The Face / 1983 54 Michael Jackson / Time / 1984 55 Madonna / Time / 1985 56 David Bowie / Vanity Fair / 1986 57 Cyndi Lauper / Details / 1989 58 Madonna / Vanity Fair / 1986 59 Stevie Wonder / Interview / 1986 60 Michael Jackson / Rolling Stone / 1987 61 Michael Jackson / Vanity Fair / 1989 62 Dolly Parton / Vanity Fair / 1991 63 Cyndi Lauper / Details / 1989 64 Red Hot Chili Peppers / Rolling Stone / 1992 65 Dr. Dre / The Source / 1992 66 Kurt Cobain (Nirvana) and Courtney Love (Hole) / Sassy / 1992 67 Ice T / Rolling Stone / 1992 68 Treach / Vibe / 1992 69 J Mascis (Dinosaur Jr. / Ray Gun / 1993 70 Janet Jackson / Rolling Stone / 1993 71 Snoop Dogg / Vibe / 1993 72 K.D. Lang / Vanity Fair / 1993 73 Tina Turner / Vanity Fair / 1993 74 Mick Jagger / Esquire / 1993 75 Tupac Shakur / Vibe / 1994 76 Marilyn Manson / Rolling Stone / 1997 77 Notorious B.I.G. / Rap Pages / 1997 78 Jay-Z / Blaze / 1999 79 Britney Spears / Rolling Stone / 1999 80 Alanis Morissette / Yahoo! Internet Life / 2000 81 Eminem / Spin / 2001 82 Dixie Chicks / Entertainment Weekly / 2003 83 Brandy / Vibe / 2004 84 Bono / New York Times Magazine / 2005 85 Tupac Shakur, Jam Master Jay, Notorious B.I.G. / Vibe / 2005 86 Kanye West / Rolling Stone / 2006 87 Snoop Dogg / Rolling Stone / 2006 88 Christina Aguilera / Marie Claire / 2008 89 Justin Bieber / Complex / 2012 90 Katy Perry / The Hollywood Reporter / 2012 91 Lady Gaga / Vanity Fair / 2012 92 Paul McCartney / Clash / 2012 93 One Direction / Wonderland / 2012 94 Prince / V / 2013 95 Beyoncé / GQ / 2013 96 Justin Timberlake / T / 2013 97 Miley Cyrus / Rolling Stone / 2013 98 Rihanna / GQ / 2013 99 Questlove (The Roots) / Wired / 2014 100 Pharrell / Billboard / 2014 101 Kanye West and Kim Kardashian / Vogue / 2014