Last updated on June 24th, 2024 at 12:45 am

There’s cool, and then there’s the timeless “old-school cool.”

Whether it’s the punks of the 1980s or sophisticates from the 1880s, each period has its own version of cool.

Let’s take a moment to reminisce about the rad, the awesome, and the awe-inspiring figures from the past

Susan Kare, famous Apple artist who designed many of the fonts, icons, and images for Apple, NeXT, Microsoft, and IBM. (1980s)

The Three Stooges visiting Yellowstone in 1969.

The Undertaker poses with an older woman, c. 1990s

Phil Collins in the 1990s.

Epic 80s moments

Uncle and Nephew playing poker, c. 1978.

Dolly Parton, 1970s

Burlington Mayor Bernie Sanders picks up trash on his own in a public park after being elected in 1981.

Carrie Fisher feeds Meryl Streep chocolate cake, 1991

Mark Hamill and Annie Potts on the set of Corvette Summer, 1978.

Heading to a concert in 1977.

A young Phil Collins in the 1960s.

Sarah Jessica Parker, Rob Lowe, and Robert Downey Jr. at the Governors Ball, 1988.

Prince stands victorious over Charlie Murphy during a game of basketball, 1985.

Heath Ledger’s Polaroid selfie with Larisa Oleynik, Joseph Gordon-Levitt and Julia Stiles on the set of 10 Things I Hate About You, 1999.

Hippie dad walking with his daughter. Amsterdam,1968

A 17-year-old’s yearbook photo, 1970s.