Mike
There’s nothing like a dose of nostalgia to remind you how effortlessly cool some celebrities were back in the day—or, in some cases, before they even knew what cool was.
The r/OldSchoolCool subreddit is a treasure trove of iconic photos, capturing stars at their peak or in those candid, early moments before fame hit.
Whether it’s classic Hollywood glam, 70s rockstar vibes, or vintage snapshots of future legends, these pictures are a perfect blend of history and swagger.
Here’s a collection of the coolest old-school cool celebrity moments we found this week—enjoy the trip back in time.
1. Bettie Page at the beach (1953)
2. Joe Pesci at 14 years old, 1957
3. Mike Tyson with his Rolls Royce in 1987
4. Happy Birthday Marisa Tomei. Here she is in the 90s.
5. Behind the scenes of the “original” Star Wars movie.
6. Winona Ryder at the premiere of Bram stoker’s dracula – 1992
7. Michelle Pfeiffer, early 80’s
8. Andre the Giant in 1982
9. Polaroid for a casting of Salma Hayek, 1995
10. Princess Grace of Monaco visiting JFK at the White House, 1961
11. Susan Sarandon 1970s
12. Tom Morello watching a Tool show in 1991
13. Marilyn Monroe without makeup. 1955
14. Stephen Hawking and his wife Jane on their wedding day (1965)
15.
16. Brigitte Bardot and Pablo Picasso. 1950s
17. Elizabeth Hurley as an 18 year old goth, 1984
18. Track olympic Athlete Florence “FloJo” Griffith Joyner training in 1988.
19. Richard Nixon at age 17, 1930
20. Behind the scenes – Aliens (1986)
21. old polaroid of Winona Ryder and (I think) Robert Sean Leonard in the very early 1990s
22. Six feet tall aspiring actress, Sigourney Weaver, 1979
23. Pamela Anderson, 1993
24. Jennifer Aniston, bts on the set of Leprechaun, 1993
25. Julie Newmar, 1960
26. A Young Katey Sagal 1980s
27. Sophia Loren as Cleopatra (1954)
28. David Bowie and Joan Jett in 1989
29. Actor Mads Mikkelsen’s high school graduation photo 1980s
30. Cherilyn Sarkisian’s mugshot, better know as Cher, when she was 13 y/o for “borrowing” a friend’s car – 1959
31. Hans Zimmer and Moog Synthesizer 1981
32. John Belushi , Carrie Fisher & Dan Aykroyd on the set of The Blues Brothers (1980)
33. Laura Linney in 1995
34. Martina Hingis winning in the ’90s
35. Roger Moore and Christopher Walken behind the scenes for A View to Kill (1985)
