r/OldSchoolCool • • 5h ago

srael "IZ" Kamakawioʻole, famous for Somewhere Over The Rainbow, having one of his last performances before his passing in 1997

9.0k Upvotes

r/OldSchoolCool • • 12h ago

1936 in London. Jesse Owens carrying home four gold medals for America in the Olympics.

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10.8k Upvotes

r/OldSchoolCool • • 8h ago

One of the baddest mofos alive. Rosey Grier, football player, body guard, minister, seen here showing men how to do needlepoint in 1973.

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1.5k Upvotes

Rosey Grier played in the NFL for 12 seasons for the Giants then the Rams. He was Ethel Kennedy's bodyguard and it was he who got the gun from Sirhan Sirhan when Robert F. Kennedy was shot. He made a book called "Needlepoint for Men" in 1973 (this photo is from that book). He became a Protestant minister in 1983. He is alive and well today. He turned 94 in July.


r/OldSchoolCool • • 3h ago

The Flaming Lips play Pennyroyal Tea six months after Cobain’s death. (1994)

349 Upvotes

r/OldSchoolCool • • 16h ago

1960s Paul Newman in Venice, 1963. How cool is this?

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3.0k Upvotes

r/OldSchoolCool • • 18h ago

1960s Born on this date in 1938, German singer, actress, model, and Velvet Underground collaborator Nico (1966)

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2.0k Upvotes

r/OldSchoolCool • • 7h ago

Ram Jam - Black Betty (1977) Full HD (Digitally Remastered and Upscaled) - (1080p, h264)

254 Upvotes

r/OldSchoolCool • • 20h ago

1930s Randolph Scott and Cary Grant relaxing by the pool at their Santa Monica beach house nicknamed "Bachelor Hall" in 1935.

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3.0k Upvotes

Their close companionship and long periods of cohabitation - spanning off and on for over a decade while both actors also married women - have long fueled pop culture fascination and biographical speculation regarding the nature of their relationship.


r/OldSchoolCool • • 18h ago

Mike Tyson introduces Marvis Frazier to the uppercut, 1986

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1.7k Upvotes

r/OldSchoolCool • • 9h ago

1960s Nina Simone - c.1969

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242 Upvotes

r/OldSchoolCool • • 10h ago

1960s Wilson Picket & Duane Allman - Muscle Shoals, AL - November, 1969

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240 Upvotes

r/OldSchoolCool • • 22h ago

The Grassroots - Let's Live For Today - 1967

1.2k Upvotes

r/OldSchoolCool • • 8h ago

1800s Oscar Wilde in a fancy ball costume during his college days at Magdalen College, Oxford. May 1878

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83 Upvotes

r/OldSchoolCool • • 9h ago

Run DMC (and posse) - Hollis, Queens - c. 1984

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114 Upvotes

r/OldSchoolCool • • 9h ago

1990s Just two old souls, discussing the finer points of life, ca. 1996, and the universe foreshadowing the lengthy curls I have today, ca. 1998

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91 Upvotes

r/OldSchoolCool • • 1d ago

1990s Sigourney Weaver and Winona Ryder, 1997.

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14.1k Upvotes

r/OldSchoolCool • • 3h ago

My grandmother beat Bill Cosby in a coed doubles tennis match 1976

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33 Upvotes

Paducah, Ky. Was told he was furious he lost to women.


r/OldSchoolCool • • 4h ago

1980s Michael Hedges -Aerial Boundries 1986

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19 Upvotes

r/OldSchoolCool • • 21h ago

A young lady with her cat, her Cannabis plant and the August 15, 1915, edition of the French weekly newspaper Le Miroir.

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438 Upvotes

r/OldSchoolCool • • 11h ago

Helsinki 1930s

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65 Upvotes

r/OldSchoolCool • • 1d ago

Shelley Fabares In The 1965 Film “Happy Girl” Alongside Elvis Presley.

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1.0k Upvotes

r/OldSchoolCool • • 1d ago

(1989) Anything smoother than when Stevie Ray Vaughan busted a string and changed guitars mid song?

1.7k Upvotes

r/OldSchoolCool • • 7h ago

The Main Ingredient - Everybody Plays the Fool (1972)

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26 Upvotes

r/OldSchoolCool • • 1d ago

Tobey Maguire & Dewey on the set of Cider House Rules in 1999.

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2.8k Upvotes

r/OldSchoolCool • • 1d ago

Osaka Castle overlooking Nippon Life field during a night game in 1960.

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1.4k Upvotes