1. Justin Timberlake (2003)
This was Justin’s first solo photo shoot for the magazine. This cover photo was shot in the emptied out pool of the L.A.’s Ambassador Hotel.
2. Jennifer Aniston (1996)
This was Jennifer’s first solo cover for the magazine, but not her first time on the cover. She had appeared the previous year with her Friends costars.
3. Blake Lively Leighton Meester (2009)
“We’re very close. We’re friends. I can’t even remember a reason why people would say we are not,” Leighton told Rolling Stone in the interview.
4. Britney Spears (1999)
Britney was 17 years old when she posed for the iconic “Lolita” cover.
5. David Duchovny and Gillian Anderson (1996)
A memorable cover to X-Files fans everywhere, inside the issue David and Gillian are also in bed with series creator Chris Carter.
6. Janet Jackson (1993)
One the most iconic photos ever taken of Janet. Also, the hands cupping her breasts belonged to her then-husband Réne Elizondo.
7. Cindy Crawford (1994)
This cover was shot by the late L.A. photographer, Herb Ritts.
8. Gavin Rossdale (1996)
At the time British band Bush was so popular in the U.S. that Gavin easily landed a cover, in UK however the band still remained virtually unknown.
9. Lisa Bonet (1988)
This cover took many people by surprise, Lisa’s image was that of her wholesome Denise Huxtable character on The Cosby Show. In 1988 it was an image she was eager to shed.
10. Brad Pitt (1994)
This was Brad’s first time on the cover.
11. Sarah Michelle Gellar (1998)
In the issue Sarah spoke about some of the initial lack of enthusiasm from the network about Buffy, saying, “You try being on a midseason replacement show on the WB called Buffy the Vampire Slayer and see how much respect you get.”
12. Jennifer Love Hewitt (2002)
This was not Jennifer’s first solo cover for the magazine. Her first solo cover was on the May 1999 issue.
13. Cameron Diaz (1996)
Cameron admits in the interview that she didn’t know she was working on a high-profile movie when filming The Mask, halfway through filming she asked, “Is there any place my friends and family can see this movie?”
14. Jessica Alba (2005)
“The scripts I get are always for the whore, or the motorcycle chick in leather, or the horny maid … I don’t think this is happening to Natalie Portman,” Jessica complained to the magazine.
15. Angelina Jolie (1999)
This was Angelina’s first cover and it was just as her career was taking off. Inside Rolling Stone got it right when they called her “Hollywood’s next great bombshell.”
16. Uma Thurman (1989)
The then-19 year old Uma, landed the cover following her breakthrough role in Dangerous Liaisons.
17. Go-Go’s (1982)
This cover was actually recreated in 2008 with the cast of The Hills.
18. Winona Ryder (1994)
This was Winona’s second cover; she appeared on her first cover three years earlier on the annual “Hot Issue.”
19. Gisele Bündchen (2000)
“I don’t wear transparent,” Gisele told the magazine. “If the designers ask me to wear see-through, I say no. I simply won’t do it. I don’t feel comfortable about people seeing my nipples.”
20. Rosario Dawson and Rose McGowan (2007)
Rosario revealed that in order to get the shot right, “She [Rose] actually had to be on an apple box to make sure that our butts touched and our shoulders touched.”
21. Christina Aguilera (2002)
In the interview with the magazine, Christina said “Xtina has come out, she’s showing her colors now.”
22. Evangeline Lilly (2005)
In the interview Lilly revealed that she didn’t have a lot of inhibitions, telling a story of how she peed in a garage can in front of her Lost costars on a dare.
23. Laetitia Casta (1998)
French model Laetitia Casta, is best known as one of the first Victoria’s Secret Angels.
24. Spice Girls (1997)
The ages of the Spice Girls when they shot this cover: Scary (22), Baby (21), Posh (22), Ginger (24), and Sporty (23).
25. Britney Spears (2003)
Rolling Stone posed the question: Do people still care about the music? Or is she becoming more famous for stunts [her VMA Kiss with Madonna] like this?
“I’m not gonna come out on this record [In the Zone] and show my crotch or anything,” Britney responded. “That’s not me. I would never do anything like that. It’s all in the way you do stuff, all in the way you carry things. The music is most important to me.”
Honorable mention: Carrie Fisher dressed as Princess Leia in the slave bikini (1983).
“For Rolling Stone’s 1983 summer double issue, Aaron Rapoport staged a lighthearted beach romp with a fuzzy Ewok, a tusked Gamorrean Guard, the evil Darth Vader and, in a now-notorious revealing metal bikini, Carrie Fisher working it as every early-Eighties adolescent boy’s dream, Princess Leia Organa. Fisher’s accompanying Q&A is hilarious.”
Summary via: Rock Paper Photo.