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Jake's Jackpot
Exploring past decades through advertising, artwork, photography, and print that captured the pop culture of the time. Discover more in our store.

Artwork

24
Colorful caricature of John Cougar Mellencamp holding an acoustic guitar against a yellow rural landscape with a small farmhouse in the background.
1980sArtworkCelebrity

John Cougar Mellencamp Illustration – 1987

by Admin October 10, 2026
Colorful illustrated collage featuring an orange New York-style taxi, playing cards, a train, running figures, and a large woman’s face.
1960sArtwork

‘Somebody Owes Me Money’ Illustration – 1969

by Admin October 7, 2026
Detailed painted portrait of Johnny Cash wearing a dark jacket, white open collar and patterned scarf against a dark brown background.
1970sArtworkCelebrity

Johnny Cash Illustration – 1970

by Admin October 4, 2026
Surreal illustration of a dark snakeskin-patterned book titled “Holy Terror,” with gold-edged pages and a red ribbon bookmark shaped like a forked tongue.
1980sArtwork

Holy Terror – Illustration by Eraldo Carugati – 1982

by Admin September 27, 2026
Satirical illustration of Uncle Sam relaxing in a golf cart with a drink and golf clubs above the words “Uncle Sam Desires You.”
1970sArtwork

“Uncle Sam Desires You” Satirical Illustration – 1975

by Admin September 27, 2026
Black-and-white caricature illustration of Aaron Neville singing into a microphone while holding percussion instruments.
1990sArtworkCelebrity

Aaron Neville – Illustration by David Levine – 1990

by Admin September 27, 2026
Surreal illustration by Jean-Michel Folon showing a giant orange crab between tall blue walls while winged human-like figures fly overhead.
1970sArtwork

The Eden Express Illustration, Jean-Michel Folon – 1975

by Admin September 27, 2026
1979 illustration of Marilyn Monroe in a black dress posed in front of a stylized version of Vincent van Gogh’s The Starry Night.
1970sArtworkCelebrity

Marilyn Monroe – Illustration by Dennis Magdich – 1979

by Admin September 24, 2026
Pat Andrea painting depicting Brandon Teena as a stylized figure with an oversized male head and female figure positioned alongside it.
1990sArtwork

Brandon Teena — Death of a Deceiver, Pat Andrea, 1995

by Admin September 24, 2026
Color caricature illustration of Dolly Parton and Burt Reynolds riding in a black sports car, created by Chuck Slack in 1982.
1980sArtwork

The Best Little Whorehouse in Texas — Dolly Parton & Burt Reynolds, 1982

by Admin September 24, 2026
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  • Gas Station Caper Illustration – 1990

  • Ampex Premium Tapes ft. Blondie & Bee Gees – Print Ad – 1980

  • Marilyn Monroe – Illustration by Dennis Magdich – 1979

  • David Letterman (1987)

  • Drugstore Cowboy Cast Photo – 1997

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