Growing up in the 80s and 90s, I remember when celebrities had this untouchable cool about them—before social media, when you only saw glimpses of their lives in magazines or on MTV.
But it’s not just my childhood favorites that give me that warm, nostalgic feeling. It’s awesome to look back at photos from all eras and see stars at the peak of their coolness.
Whether it’s Steve McQueen looking like he just stepped out of an action movie or Winona Ryder being the ultimate 90s icon, these old school cool pics are like a time capsule of pure charisma. Here’s what we found this time around.
1. August 24, 1997 a week before her death. Princess Diana.
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2. Maggie Smith (ca. 1960)
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3. My uncle at a party with Nirvana just before they became famous (1991)
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4. Dance teacher Patsy Swayze, center, with her daughter-in-law Lisa Niemi and son Patrick Swayze, 1978
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5. Marisa Tomei’s yearbook from 1982
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6. James Earl Jones in 1961 – RIP
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7. Jason Momoa in the 90s
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8. Carrie Fischer Trying On Harrison Ford’s Glasses (1980s)
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9. Picture of me(Right) and Tupac Shakur, 1993
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10. My mom and coolio in the 90s 30 seconds after he asked my mom to leave my dad to go on tour.
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11. Amy Winehouse at her grandmother’s home in 1999.
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12. Leonardo DiCaprio & Charlize Theron at her 22nd Birthday Party, 1997
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13. Julia Louis-Dreyfus and Brad Hall on their wedding day in 1987
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14. Susanna Hoffs of the Bangles with her husband Jay Roach (director of the Austin Powers movies) in 1993 and 2020. They have been happily married for 31 years.
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15. When Mick Jagger and his girlfriend Marianne Faithfull met Alain Delon in 1967
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16. Kirsten Dunst in her bedroom 1997
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17. Gorgeous Kate Winslet in the 90s
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18. Tara Reid in an American Pie screen test, 1998
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19. Tears for Fears in 1985 vs. 2023
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20. In honour of father’s everywhere, here’s John Goodman with his daughter in 1990
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21. Heath Ledger’s Polaroid selfie with Larisa Oleynik, Joseph Gordon-Levitt and Julia Stiles on the set of 10 Things I Hate About You. (1999)
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22. Teri Garr 1974
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23. Kevin Bacon and his wife Kyra, photographed with their son in the 90s
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24. Actress Sophia Loren in 1955
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25. Mila Jovovich at the premiere of the Fifth Element, 1997
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26. When Johnny Cash introduced the 13 year old singer, Dolly Parton, on the Grand Ole Opry in 1959, she got 3 encores.
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27. Jayne Mansfield posing with Miss Hollywood, 1957.
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28. Chi Chi Rodriguez and his caddie, Carl Howard, at the 75’ masters.
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29. Kris Kristofferson comforting Sinéad O’Connor after getting booed (1992)
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30. Priscilla Presley, 1975
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31. In 1999, a moderately successful Manhattan executive chef submitted an unsolicited essay entitled Don’t Eat Before Reading This to the New Yorker magazine. It transformed him into a highly successful writer and television personality.
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32. Obama and his mom, 1980s
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33. Michelle Burke, Jason London, and Joey Lauren Adams on the set of Dazed and Confused (1993)
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34. Gary Oldman and Natalie Portman on set of “Léon: The Professional”, 1994
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35. A before-Wonder Woman Lynda Carter, 1970s.
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36. Prince stands silently sucking his lollipop during the song “We Are The World” at the American Music Awards, 1995.
Mike Primavera is a Chicago-based comedy writer even though he doesn't HAVE to work. He lives comfortably off of his family's pasta fortune. Follow him on all social media at @primawesome