#oldschoolcool
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1906 - San Francisco - Presidio soldiers law enforcement
Credit to the original poster P_a_s_g_i_t_21 who posted this on r/OldSchoolCool on October 5th, 2026 at 5:54 PM UTC.
October 5, 2026 at 6:11 PM
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From the OldSchoolCool community on Reddit: The Notorious B.I.G. outside his mother’s house in in January 1995
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October 5, 2026 at 5:54 PM
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Santa Cruz, 1984.
Credit to the original poster CloakOfElvenkind who posted this on r/OldSchoolCool on October 5th, 2026 at 5:12 PM UTC.
October 5, 2026 at 5:41 PM
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Happy 80th Birthday Susan Sarandon (pics 1 & 2 of 34 year old Susan from 1980)
Credit to the original poster Sashamelanie who posted this on r/OldSchoolCool on October 5th, 2026 at 5:08 PM UTC. Credit to the original poster Sashamelanie who posted this on r/OldSchoolCool on October 5th, 2026 at 5:08 PM UTC. Credit to the original poster Sashamelanie who posted this on r/OldSchoolCool on October 5th, 2026 at 5:08 PM UTC. Credit to the original poster Sashamelanie who posted this on r/OldSchoolCool on October 5th, 2026 at 5:08 PM UTC.
October 5, 2026 at 5:21 PM
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A female gunslinger from the Golden West, 1906
photo: e.w. kelly Credit to the original poster No-Incident-6913 who posted this on r/OldSchoolCool on October 5th, 2026 at 4:43 PM UTC.
October 5, 2026 at 4:51 PM
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My Dad 62-63 USS Nitro
My Dad 62-63 USS Nitro Credit to the original poster Chad59N who posted this on r/OldSchoolCool on October 5th, 2026 at 4:28 PM UTC.
October 5, 2026 at 4:41 PM
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Random 1930s footage, Chicago remastered
Credit to the original poster Expensive-Course3030 who posted this on r/OldSchoolCool on October 5th, 2026 at 4:02 PM UTC.
October 5, 2026 at 4:31 PM
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Anybody remember Autobuff Magazine ? 1986
Credit to the original poster Epstiendidntkillself who posted this on r/OldSchoolCool on October 5th, 2026 at 3:49 PM UTC.
October 5, 2026 at 4:11 PM
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Happy 51st Birthday Kate Winslet (born Oct 5, 1975)
Credit to the original poster Sashamelanie who posted this on r/OldSchoolCool on October 5th, 2026 at 3:33 PM UTC. Credit to the original poster Sashamelanie who posted this on r/OldSchoolCool on October 5th, 2026 at 3:33 PM UTC. Credit to the original poster Sashamelanie who posted this on r/OldSchoolCool on October 5th, 2026 at 3:33 PM UTC. Credit to the original poster Sashamelanie who posted this on r/OldSchoolCool on October 5th, 2026 at 3:33 PM UTC.
October 5, 2026 at 3:51 PM
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Me Xmas 88 10 yrs old, best parents ever got me the best gift ever….my Dyno Compe ❤️
Credit to the original poster Wantavant who posted this on r/OldSchoolCool on October 5th, 2026 at 3:03 PM UTC.
October 5, 2026 at 3:21 PM
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Me coming home from school, 1999
Credit to the original poster Educational_Piece777 who posted this on r/OldSchoolCool on October 5th, 2026 at 2:50 PM UTC.
October 5, 2026 at 3:01 PM
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Italian partisans planning a patrol. Castelluccio area, Italy, 5 October 1944
Credit to the original poster HeStoleMyBalloons who posted this on r/OldSchoolCool on October 5th, 2026 at 1:40 PM UTC.
October 5, 2026 at 2:51 PM
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Metallica late 80s
Credit to the original poster Dogcoolerthanhuman who posted this on r/OldSchoolCool on October 5th, 2026 at 12:12 PM UTC.
October 5, 2026 at 12:31 PM
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Youth people, Ukraine, Lviv, 1970s. Photographer Vili Furgalo
Credit to the original poster No-1nternet who posted this on r/OldSchoolCool on October 5th, 2026 at 11:22 AM UTC. Credit to the original poster No-1nternet who posted this on r/OldSchoolCool on October 5th, 2026 at 11:22 AM UTC. Credit to the original poster No-1nternet who posted this on r/OldSchoolCool on October 5th, 2026 at 11:22 AM UTC. Credit to the original poster No-1nternet who posted this on r/OldSchoolCool on October 5th, 2026 at 11:22 AM UTC.
October 5, 2026 at 11:41 AM
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My mum with her 80s perm
Credit to the original poster Idonthavemanyfriend who posted this on r/OldSchoolCool on October 5th, 2026 at 10:41 AM UTC.
October 5, 2026 at 10:51 AM
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The Notorious B.I.G. outside his mother’s house in in January 1995
Credit to the original poster SappyGilmore who posted this on r/OldSchoolCool on October 5th, 2026 at 9:41 AM UTC.
October 5, 2026 at 10:11 AM
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top: my mom 1975,me 1992, bottom : daughter Remi 2010, misc vogue mags
Credit to the original poster AffectionateRain6796 who posted this on r/OldSchoolCool on October 5th, 2026 at 3:25 AM UTC.
October 5, 2026 at 3:51 AM
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One of the earliest 'selfies,' taken by the Byron Company on a New York rooftop in December 1920. The left shows how they used a mirror to frame it.
Credit to the original poster LuxRiven who posted this on r/OldSchoolCool on October 5th, 2026 at 3:03 AM UTC.
October 5, 2026 at 3:21 AM
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RIP Janis Joplin, who died 56 years ago today, on Oct. 4, 1970
Credit to the original poster TracesofTexas who posted this on r/OldSchoolCool on October 5th, 2026 at 1:51 AM UTC.
October 5, 2026 at 2:31 AM
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16-year-old Edie Sedgwick in Connecticut, 1959
Credit to the original poster Unique_Might4471 who posted this on r/OldSchoolCool on October 5th, 2026 at 1:41 AM UTC.
October 5, 2026 at 2:21 AM
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Whitney Houston who won her second Grammy at 1988 Grammy Awards.
Credit to the original poster Beginning-Passion676 who posted this on r/OldSchoolCool on October 5th, 2026 at 1:40 AM UTC.
October 5, 2026 at 2:11 AM
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In 1981, Men At Work released Who Can It Be Now
Credit to the original poster Mad_Season_1994 who posted this on r/OldSchoolCool on October 5th, 2026 at 1:37 AM UTC.
October 5, 2026 at 2:01 AM
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Four women on a beach in Florida show the latest in swimsuit fashion, photo by Nina Leen for LIFE magazine, May 1950
Credit to the original poster Gothic-Fan85 who posted this on r/OldSchoolCool on October 5th, 2026 at 1:37 AM UTC.
October 5, 2026 at 1:51 AM
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The Offspring - Pretty Fly (For A White Guy) live 1999
Credit to the original poster FrenchieMama807 who posted this on r/OldSchoolCool on October 5th, 2026 at 1:17 AM UTC.
October 5, 2026 at 1:31 AM
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Blondie - 1976
Gary Valentine, Clem Burke, Debbie Harry, Chris Stein, Jimmy Destri Credit to the original poster RadioStar1211 who posted this on r/OldSchoolCool on October 5th, 2026 at 12:49 AM UTC.
October 5, 2026 at 1:11 AM