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r/OldSchoolCool

18,594,680 subscribers

Notice: This subreddit is not actively monitored, so the posts here are only a small subset of what exists on reddit.

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to r/OldSchoolCool by Seraphenigma
1 month ago
Preview thumbnail for Keanu Reeves hanging out with a homeless man in West Hollywood (1997) image
Keanu Reeves hanging out with a homeless man in West Hollywood (1997)
to r/OldSchoolCool by anwar_idr
1 month ago
Preview thumbnail for Dolly Parton towards the beginning of her career, circa 1966 image
Dolly Parton towards the beginning of her career, circa 1966
1960s
to r/OldSchoolCool by anwar_idr
1 month ago
Preview thumbnail for Jim Carrey during his first lead role on the short-lived TV series The Duck Factory in 1984 image
Jim Carrey during his first lead role on the short-lived TV series The Duck Factory in 1984
1980s
to r/OldSchoolCool by Lepke2011
1 month ago
Preview thumbnail for Bard Pitt's Senior Prom Photo at Kickapoo High School in Springfield, Missouri, 1981. image
Bard Pitt's Senior Prom Photo at Kickapoo High School in Springfield, Missouri, 1981.
1980s
in Springfield, MO
to r/OldSchoolCool by anwar_idr
1 month ago
Preview thumbnail for Johnny Depp getting a tattoo at Fun City Tattoo in New York, 1993 image
Johnny Depp getting a tattoo at Fun City Tattoo in New York, 1993
1990s
in New York City
to r/OldSchoolCool by bluemarvel99
3 months ago
Preview thumbnail for Is The "Dream Team" Still The Greatest International Basketball Team Ever Assembled? (1992) image
Is The "Dream Team" Still The Greatest International Basketball Team Ever Assembled? (1992)
1990s
to r/OldSchoolCool by j3434
3 months ago
Preview thumbnail for Living the dream and didn't even realize it. The 70s image
Living the dream and didn't even realize it. The 70s
1970s
to r/OldSchoolCool by singatermelon
3 months ago
Preview thumbnail for One of the first women helicopter pilots skydiving for fun (1965) image
One of the first women helicopter pilots skydiving for fun (1965)
to r/OldSchoolCool by malist42
3 months ago
Preview thumbnail for Is 1984 Old School? image
Is 1984 Old School?
to r/OldSchoolCool by EdwardBliss
3 months ago
Preview thumbnail for Ann and Nancy Wilson from Heart, 1977 image
Ann and Nancy Wilson from Heart, 1977
1970s
to r/OldSchoolCool by FewCap982
3 months ago
Preview thumbnail for Tupac’s Last Photograph. September 7, 1996 image
Tupac’s Last Photograph. September 7, 1996
1990s
to r/OldSchoolCool by Corpsman223
3 months ago
Preview thumbnail for The incomparable, Madeline Kahn with, Mel Brooks, who despite not having conventional leading man stature and looks, always ended up in the arms of the most beautiful women in the world. 1977. image
The incomparable, Madeline Kahn with, Mel Brooks, who despite not having conventional leading man stature and looks, always ended up in the arms of the most beautiful women in the world. 1977.
1970s
to r/OldSchoolCool by BlackPantherDies
3 months ago
Preview thumbnail for My father training as a priest in his mid twenties - around 1978 image
My father training as a priest in his mid twenties - around 1978
1970s
to r/OldSchoolCool by LuunchLady
3 months ago
Preview thumbnail for Vincente Minnelli and Judy Garland with their daughter Liza Minnelli, 1965 image
Vincente Minnelli and Judy Garland with their daughter Liza Minnelli, 1965
1960s
to r/OldSchoolCool by RiverHistorical8933
3 months ago
Preview thumbnail for 18 year old inventor, H. Day, wearing headphones attached to a wireless under his top hat. [May 1922] image
18 year old inventor, H. Day, wearing headphones attached to a wireless under his top hat. [May 1922]
1920s
to r/OldSchoolCool by simagus
2 months ago
Preview thumbnail for [1969] Elizabeth Montgomery as Samantha Stephens image
[1969] Elizabeth Montgomery as Samantha Stephens
1960s
to r/OldSchoolCool by Amazing-Taste-1991
4 months ago
Preview thumbnail for My GG, Around 1910 image
My GG, Around 1910
1910s
to r/OldSchoolCool by man_in_search_of
1 month ago
Preview thumbnail for Phil Collins at Live Aid (July 1985) image
Phil Collins at Live Aid (July 1985)
1980s
to r/OldSchoolCool by Jaguars4life
3 months ago
Preview thumbnail for [1995] The 2024 Baseball Hall of Fame induction ceremony is less than 10 days away! And recently I was able to find on YouTube most of the 1995 Hall of Fame Ceremony including the induction speech of the GOAT 3rd baseman Mike Schmidt! 45:00 in the video is where the induction ceremony starts image
[1995] The 2024 Baseball Hall of Fame induction ceremony is less than 10 days away! And recently I was able to find on YouTube most of the 1995 Hall of Fame Ceremony including the induction speech of the GOAT 3rd baseman Mike Schmidt! 45:00 in the video is where the induction ceremony starts
1990s
to r/OldSchoolCool by DarkAmbivertQueen
4 months ago
Preview thumbnail for Janet in Japan for cellphone commercials in 1993 image
Janet in Japan for cellphone commercials in 1993
1990s
in Japan
to r/OldSchoolCool by Creepy_Pea_5472
3 months ago
Preview thumbnail for Boricuas family 1983 image
Boricuas family 1983
1980s
to r/OldSchoolCool by Human_Influence_391
4 months ago
Preview thumbnail for Parents first selfie on their new camera (1998) image
Parents first selfie on their new camera (1998)
to r/OldSchoolCool by goxilo
4 months ago
Preview thumbnail for My late father in law, around 20 years old in the late 1960s. Spent 20 years in the US Navy. image
My late father in law, around 20 years old in the late 1960s. Spent 20 years in the US Navy.
1960s
to r/OldSchoolCool by kaljaraska
4 months ago
Preview thumbnail for My wife said i couldn't pull it off (update 6 years in the making) circa 1990 and now image
My wife said i couldn't pull it off (update 6 years in the making) circa 1990 and now
to r/OldSchoolCool by Remarkable-Bowl-9161
4 months ago
Preview thumbnail for On this day 55 years ago Brian Jones, the founder of The Rolling Stones, drowned in his pool aged 27 image
On this day 55 years ago Brian Jones, the founder of The Rolling Stones, drowned in his pool aged 27