/r/OldSchoolCool - top ten submissions for each month of 2025

sfw subreddits | << OldSchoolCool 2024

2025, June

John F. Kennedy smoking a cigar. He’d buy 1,200...

59367 John F. Kennedy smoking a cigar. He’d buy 1,200...

My Grandpa, one of the designers on the Dodge V...

52883 My Grandpa, one of the designers on the Dodge V...

My mom around 1963 in the Mojave Desert.

36719 My mom around 1963 in the Mojave Desert.

a young man caring for his grandfather, 1974

32508 a young man caring for his grandfather, 1974

Lamborghini Countach on Beach Blvd., 1990

29889 Lamborghini Countach on Beach Blvd., 1990

John Travolta, Phil LaMarr (Marvin) and Samuel ...

25013 John Travolta, Phil LaMarr (Marvin) and Samuel ...

Roger Troutman showing off his talk box skills ...

20730 Roger Troutman showing off his talk box skills ...

Don Rickles’ prank on Frank Sinatra (The Tonigh...

12680 Don Rickles’ prank on Frank Sinatra (The Tonigh...

This is my mom in the 70s when it was still the...

11853 This is my mom in the 70s when it was still the...

Married couple Mildred and Richard Loving in th...

9362 Married couple Mildred and Richard Loving in th...

2025, May

My mother in 1991

87747 My mother in 1991

17 to 60

In an attempt to balance out all the “would you...

18466 In an attempt to balance out all the “would you...

When I was a baby my mom made us matching party...

18018 When I was a baby my mom made us matching party...

my dad made sure I never had to miss out on fri...

17923 my dad made sure I never had to miss out on fri...

My late mom in 1972. Hippie, mom to 7, calculus...

14412 My late mom in 1972. Hippie, mom to 7, calculus...

My Grandpa in 1955

10549 My Grandpa in 1955

My visitations with dad (parents divorced) was ...

10271 My visitations with dad (parents divorced) was ...

Michael Caine and Shakira Baksh; on their weddi...

9694 Michael Caine and Shakira Baksh; on their weddi...

My Brother In Law getting slimed at Universal S...

9603 My Brother In Law getting slimed at Universal S...

2025, April

1979. 13th Birthday. Mom made me the best cake ...

56017 1979. 13th Birthday. Mom made me the best cake ...

Gary Sinise here. I was going through some old ...

55297 Gary Sinise here. I was going through some old ...

1979 - my middle school bus driver was the coolest

45421 1979 - my middle school bus driver was the coolest

Me turning 23, 1976

44267 Me turning 23, 1976

My grandfather, 1975

23106 My grandfather, 1975

Walton Goggins, high school senior, 1989.

18482 Walton Goggins, high school senior, 1989.

Sigourney Weaver and Winona Ryder, 1997

15196 Sigourney Weaver and Winona Ryder, 1997

Princess Diana hugging a young fan in Birmingha...

12984 Princess Diana hugging a young fan in Birmingha...

Joel McHale and his wife Sarah in the 90s

10216 Joel McHale and his wife Sarah in the 90s

Tom Hanks in Beaufort, SC, Sept. 11, 1993. Mary...

9559 Tom Hanks in Beaufort, SC, Sept. 11, 1993. Mary...

2025, March

Kris Kristofferson tells Sinéad O'Connor ‘Don't...

50170 Kris Kristofferson tells Sinéad O'Connor ‘Don't...

A man with his dog in the 1920s

49935 A man with his dog in the 1920s

A man begging for his wife's forgiveness inside...

41934 A man begging for his wife's forgiveness inside...

My mom, age 17, late 1960s

36795 My mom, age 17, late 1960s

My mom having a drink with some British guy in ...

36253 My mom having a drink with some British guy in ...

A 16 year old girl takes this picture at a Quee...

34031 A 16 year old girl takes this picture at a Quee...

Love story. Couple at Woodstock, 1969 (48 hours...

31093 Love story. Couple at Woodstock, 1969 (48 hours...

‘Queen of Pinups’ Bettie Page, and her sister G...

29294 ‘Queen of Pinups’ Bettie Page, and her sister G...

My parents in the 1970s and in their 70s ??

29056 My parents in the 1970s and in their 70s ??

Pamela Anderson draped in a Canadian flag, 1999...

23172 Pamela Anderson draped in a Canadian flag, 1999...

2025, February

Posing for my boyfriend after our high school d...

99034 Posing for my boyfriend after our high school d...

Woman pointing a gun at a computer for some rea...

84495 Woman pointing a gun at a computer for some rea...

Rick Astley's father Ossie Astley celebrating "...

51032 Rick Astley's father Ossie Astley celebrating "...

Grace Brewster Hopper was an American computer ...

37883 Grace Brewster Hopper was an American computer ...

Mads Mikkelsen and wife Hanne Jacobsen in the l...

31666 Mads Mikkelsen and wife Hanne Jacobsen in the l...

Audrey Hepburn in her kitchen, 1950's

31498 Audrey Hepburn in her kitchen, 1950's

A glorious family photo of my parents and me fr...

26903 A glorious family photo of my parents and me fr...

Robin Williams and Shelly Duvall on the set of ...

26901 Robin Williams and Shelly Duvall on the set of ...

Half of my face looks like my great great*** gr...

26490 Half of my face looks like my great great*** gr...

Three Dutch boys, recently liberated from a Naz...

26157 Three Dutch boys, recently liberated from a Naz...

2025, January

In 1974, Masahisa Fukase photographed his wife,...

151202 In 1974, Masahisa Fukase photographed his wife,...

My parents getting me baptized by Bishop Marian...

36346 My parents getting me baptized by Bishop Marian...

EST. 1930s, North Carolina. Women of Color prot...

31344 EST. 1930s, North Carolina. Women of Color prot...

My wife’s great-grandma in 1945 Seattle

30013 My wife’s great-grandma in 1945 Seattle

My Great Grandfather getting the MOH after kill...

25081 My Great Grandfather getting the MOH after kill...

My great aunt Frida circa early 1940s. She was ...

21644 My great aunt Frida circa early 1940s. She was ...

My grandpa marrying my grandma and going off to...

20467 My grandpa marrying my grandma and going off to...

Actress Sandra Bullock at her home in 1978.

18743 Actress Sandra Bullock at her home in 1978.

Two Ottoman Wrestlers visiting New York for a w...

16298 Two Ottoman Wrestlers visiting New York for a w...

This sub liked my fascist-fighting grandfather ...

15247 This sub liked my fascist-fighting grandfather ...