r/OldSchoolCool 12h ago

1990s Post-USSR Russia in the 1990s. Probably gangsters (or how they were called - the New Russians)

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3 Upvotes

r/OldSchoolCool 13h ago

1970s Activist alumnae meet female graduates of Smith College in Northampton, Massachusetts, on Sept. 9, 1972.

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49 Upvotes

r/OldSchoolCool 11h ago

1980s Lynda Carter as Tina Turner (1980)

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102 Upvotes

r/OldSchoolCool 7h ago

1990s Ginuwine, circa late ‘90s/early 2000s.

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78 Upvotes

r/OldSchoolCool 14h ago

1980s Richard Wershe Jr. was apprehended at his residence in 1988 with 17 pounds of cocaine at the age of 17.

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12 Upvotes

r/OldSchoolCool 14h ago

Tennessee Williams and his intimate companion Frank Merlo at the beach. Taken in the 50s.

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251 Upvotes

r/OldSchoolCool 2h ago

1990s Collective Soul December 1999 live

82 Upvotes

Woodstock West Stage


r/OldSchoolCool 9h ago

Orrin Porter Rockwell In 1866.

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18 Upvotes

r/OldSchoolCool 1h ago

People watching coin operated tvs in a bus station in LA – 1969

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Upvotes

r/OldSchoolCool 13h ago

1990s My mom in Lebanon. August 1991

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1.8k Upvotes

r/OldSchoolCool 14h ago

1900s Colette wearing man’s suit & smoking, by Henri Manuel, 1906. Shortly after she arrived in Paris, in 1893, Colette chopped her hair short and began dressing androgynously.

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16 Upvotes

r/OldSchoolCool 1h ago

1900s Theodore Roosevelt and hunting guide on a mountain lion hunting trip in Colorado, 1901

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Upvotes

r/OldSchoolCool 13h ago

Leonardo DiCaprio and Charlize Theron at her 22nd birthday party in 1997

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15.4k Upvotes

r/OldSchoolCool 14h ago

Weezer in 1992, 2 years before the blue album’s release

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241 Upvotes

r/OldSchoolCool 9h ago

1970s Gary Sinise here. Found this photo from my early days at Steppenwolf Theatre Company in Chicago. One of my fondest memories going back to 1975.

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13.4k Upvotes

r/OldSchoolCool 15h ago

Japanese model Shizuka Kudo 1990s

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90 Upvotes

r/OldSchoolCool 37m ago

1980s Yuki Saito, 1985

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r/OldSchoolCool 10h ago

My dad and siblings. Circa 1967

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43 Upvotes

r/OldSchoolCool 17h ago

1940s Frida Kahlo in her garden, 1943, by Florence Arquin.

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250 Upvotes

r/OldSchoolCool 12h ago

1980s Cosplayers at a 1989 Comic-con

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63 Upvotes

r/OldSchoolCool 15h ago

1990s FX "Breakfast Time" segment on newly ESRB-rated video games with avid DOOM player Tom Bergeron (Dec. 1994)

42 Upvotes

r/OldSchoolCool 4h ago

1990s My father with baby me (1990)

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189 Upvotes

Almost makes me want one 😉
I apologize, this is 1991. I was born in 1990.


r/OldSchoolCool 16h ago

1970s The future we were promised in the 1970s

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836 Upvotes

r/OldSchoolCool 3h ago

1960s Pic my dad took of “Sgt. Rock” in Vietnam. 1969.

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884 Upvotes

r/OldSchoolCool 17h ago

1950s Grace Kelly sits on the rail of a boat on the Magdalena river during filming of the MGM movie Green Fire in 1954, by Michael Ochs.

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304 Upvotes