21 Photos Of Celebrities That Are The Definition Of Old-School Cool

Brian Roque
August 9, 2022 1.6k votes 226 voters
List Rules

Vote up your favorite old-school celebrity photos.

Photos can be seen as time capsules, giving someone a glimpse into what life could've looked like at the time the photo was taken. And, what better time to take a photo than when you meet a celebrity. From going on a date with Arnold Schwarzenegger in the '70s, to meeting Bob Ross in 1992, these photos are the epitome of “old-school cool.” Courtesy of r/OldSchoolCool.

  • Paul Rudd As A Waiter In 1990
    Photo: u/_KingPuck_ / Reddit
    1
    111 VOTES

    Paul Rudd As A Waiter In 1990

    From Redditor u/_KingPuck_:

    Paul Rudd as my aunt’s waiter at Bennigan’s in 1990.

    111 votes
  • Guest-Starring On 'Mister Rogers' Neighborhood' In 1986
    Photo: u/PolyConOne / Reddit
    2
    125 VOTES

    Guest-Starring On 'Mister Rogers' Neighborhood' In 1986

    From Redditor u/PolyConOne:

    My dad showing Mr. Rogers the process of designing toys on Mister Rogers' Neighborhood (1986).

    125 votes
  • Hanging Out With Babe Ruth In 1940
    Photo: u/Christ0naBike32 / Reddit
    3
    120 VOTES

    Hanging Out With Babe Ruth In 1940

    From Redditor u/Christ0naBike32:

    1940 - My great-great-grandma with Babe Ruth. She had a boat in New York that was docked next to his. She’s wearing his captain's hat. They were buddies. This is my favorite picture ever.

    120 votes
  • On A Date With Arnold Schwarzenegger In The '70s
    Photo: u/allaccountstakenfml / Reddit
    4
    134 VOTES

    On A Date With Arnold Schwarzenegger In The '70s

    From Redditor u/allaccountstakenfml:

    My mom and Arnold on a date in the '70s.

    134 votes
  • Army Photo With Elvis Presley In The '60s
    Photo: u/Flyerguy2014 / Reddit
    5
    130 VOTES

    Army Photo With Elvis Presley In The '60s

    From Redditor u/Flyerguy2014:

    My grandfather (right) with Elvis Presley (left) in post-war Germany. Late 1950s.

    130 votes
  • Hanging Out With Albert Einstein In 1945
    Photo: u/OGnilla / Reddit
    6
    161 VOTES

    Hanging Out With Albert Einstein In 1945

    From Redditor u/OGnilla:

    My grandma hanging out with Albert Einstein in her backyard. Taken around 1945.

    161 votes