35 Old School Cool Pics Of Celebs At The Height Of Their Coolness (April 15, 2025)

Some old photos just radiate cool—and the ones in this post have it in spades.

We’re talking old school cool pics of celebrities at the very height of their effortless charm: candid moments, behind-the-scenes snapshots, and rarely seen photos of icons hanging with fans or friends before social media made everything feel staged.

It’s pure vintage swagger, and it’ll have you saying, “They just don’t make ‘em like they used to.”

1. Dolly Parton and Carl Dean. 1964

2. Marissa Tomei’s yearbook photo in 1982

3. Pamela Anderson, 1989

4. My mum and her friend hanging out with Motörhead in 1977

5. Marilyn Monroe hitting weights in between photoshoots 1952.

6. Samuel L. Jackson and bride LaTanya at their wedding in 1980. They are still married.

7. Honoring a man who went from peanut farmer, to President, to peacemaker, Jimmy Carter. (1924-2024)

8. My mom having a drink with some British guy in Argentina (1981 or 1982)

9. Maggie Smith (ca. 1960)

10. Helen Mirren, 1970s

11. Wedding photo of Robert Smith of The Cure and wife Mary Poole in 1988. They are still married.

12. Sam Elliott and Katherine Ross in 1978 and 2023. They’ve been married for 38 years.

13. Cher 1966

14. A 16 year old girl takes this picture at a Queen concert after sneaking her camera into the concert. [1978]

15. The great Nazi killer, himself. Mr. Mel Brooks in 1944.

16. Rick Astley’s father Ossie Astley celebrating “Never Gonna Give You Up” making it to #1 on the UK charts in 1987

17. Movie Premiere in 1994 which is still considered one of the best years in Hollywood history

18. Mads Mikkelsen and wife Hanne Jacobsen in the late 90s. They have known each other for 38 years

19. Eartha Kitt drinking honey before a performance [1958]

20. Jim Carrey holding daughter Jane Erin Carrey (1987)

21. Actress Sandra Bullock at her home in 1978.

22. Joe Pesci at 14 years old, 1957

23. Pamela Anderson draped in a Canadian flag, 1999. Photo by Bryan Adams.

24. Jennifer Connelly, 1998

25. Kris Kristofferson tells Sinéad O’Connor ‘Don’t let the bastards get you down’ at Madison Square Garden, 1992

26. Danny Trejo and Antonio Banderas on the set of Desperado of 1995

27. Matthew McConaughey Mugshot 1999

28. Nicole Kidman enjoys a day out in Central Park with Isabella, her adopted daughter with Tom Cruise. 1994

29. Bettie Page at the beach (1953)

30. My Great Grandfather getting the MOH after killing Nazis in 1944 from Patton

31. Behind the scenes of the “original” Star Wars movie (1970s/80s)

32. ‘Queen of Pinups’ Bettie Page, and her sister Goldie. Photograph hand-colored by Goldie, 1950s

33. Audrey Hepburn in her kitchen, 1950’s

34. Robin Williams and Shelly Duvall on the set of Popeye, 1980.

35. Carries Fisher trying on Peter Weller’s glasses during Giorgio Armani fashion show, 1980

Mike

Mike Primavera

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