37 Vintage Photos From 1988 That Are Like a Time Machine

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Take a scroll through vintage photos from 1988: Christmas-night NES victories, brand-new boombox pride, and a kid skating the aisles of a family dry cleaners—candid scenes from real homes and shops that bring the late ’80s back to life. For context around the era, revisit our 1987 vintage photos and then jump ahead to 1990 everyday life in pictures.

1. “My pops finally beating Super Mario Bros. on Christmas night, 1988. The Nintendo was a present for ‘me and my sister.'”

A man with a beard and yellow shirt smiles and points at a retro CRT TV displaying a Thank you Mario! Your quest is over message from a classic video game. An old Nintendo console and other electronics sit on a wooden cabinet above the TV.
ThaCommittee/Reddit

2. “My grandmother and ‘Big John’ Candy. She was a secretary for the accounting firm that handled his finances. August, 1988.”

A man in a black sweater and gray pants stands next to a woman in a striped dress. They are smiling and posing for the camera in an office hallway near a wooden door.
rtisdell88/Reddit

3. “My first dance in 1988.”

A woman in a black dress and heels dances and smiles with a young boy in a suit and tie in a warmly lit, elegant room with classic furniture.
StupendousMan1995/Reddit

4. Freddie Mercury and his unimpressed cat, Tiffy, 1988

A man with a mustache sits on a couch, holding a fluffy white and gray cat. He wears a colorful shirt and looks at the camera, while the cat appears relaxed in his arms. A window with greenery is visible in the background.
redalmondnails/Reddit

5. “Me on the way to daycare in 1988.”

A young girl wearing a puffy pink jacket and white tights stands on a sunlit brick pavement, holding a small dark case. The background shows a tan brick wall and her shadow stretches behind her.
SweetPickleRelish/Reddit

6. “My dad in 1988.”

Teenager with a mullet hairstyle, sleeveless black shirt, studded gloves and belt, holding drumsticks, stands with arms crossed against a dark background, evoking an 80s rock or metal style.
thetommy4/Reddit

7. The 1988 Jamaican Bobsled Team, who were immortalized in the 1993 film ‘Cool Runnings’

Four men stand on a beach at sunset beside a bobsled, holding helmets. Three wear athletic gear with Jamaica Bobsled visible on one shirt, referencing the Jamaican bobsled team. A body of water and hills are in the background.
userdeleted/Reddit

8. Rick Astley meeting Princess Diana in 1988

A young man in a gray suit and blue tie stands next to a woman in a yellow dress jacket. They are indoors, conversing near a white pillar decorated with pink and white flowers.
Po1sonator/Reddit

9. Last day of school, 1988

A group of teenagers, some smiling and some with serious expressions, pose together outside a school building. A few hold cigarettes. Other students and buildings are visible in the background.
turn_n_2/Reddit

10. A then-unknown 18-year-old Mariah Carey meeting Will Smith, 19, at a radio concert in 1988

A young woman in a pink dress and a young man in a blue tank top hug and pose for the camera, both smiling, with a dark background behind them.
frank-darko/Reddit

11. Arnold Schwarzenegger meeting his fans in Moscow, 1988

A group of men gather closely in winter clothing, watching as a man in a gray Soviet military-style coat and hat shows them pages from a large open photo book. It appears to be evening or dusk.
SalzaMaBalza/Reddit

12. Pee Wee Herman, Valerie Golino, and Arsenio Hall in 1988

Three people stand together at an event; one holds a plaque, another wears a dark dress with curly hair, and the third wears a suit and tie. There are cameras and people visible in the background.
userdeleted/Reddit

13. “My bestie and I at our prom in 1988. Yes, those are cookies in my cleavage, and yes, she is smoking.”

Two young women sit at a table, both smoking cigarettes. One woman wears a black dress and smiles with her eyes closed, while the other wears a white jacket and looks relaxed. A plate of cookies is in front of them.
66Lightning650/Reddit

14. Nicolas Cage and Johnny Depp in 1988

Two men stand side by side at night. One wears a black leather jacket over a white shirt, and the other wears a light-colored fedora hat, a dark coat, and a dark shirt. Both look directly at the camera.
Cubelock/Reddit

15. “Spring Break, Daytona Beach 1988. Some friends and I are eating at Taco Bell.”

Three young men sit at a Taco Bell booth, surrounded by empty wrappers, drink cups, and food boxes, laughing and eating together. The table is crowded with fast food items.
dj3po1/Reddit

16. Tony Hawk in Upland, California, in 1988

A teenage skateboarder with straight blond hair holds up a skateboard vertically, wearing a graphic t-shirt, gloves, and pads. The image is in black and white and taken indoors, with several people blurred in the background.
SeoulofSoraka/Reddit

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

Three young adults dressed in formal evening wear sit at a dinner table with plates of food and drinks, posing for a photo at a glamorous event or party.
ASAmd/Reddit

18. “Me skating around my family’s dry cleaners in 1988.”

A young child stands with one foot on a skateboard inside a laundromat or dry cleaning shop, surrounded by hanging clothes and industrial laundry equipment. The scene is brightly lit and has a nostalgic feel.
d1msum4u/Reddit

19. Nirvana in 1988. A year before their first album, Bleach, was released. You’ll notice their original drummer, Chad Channing, is pictured here, as Dave Grohl wouldn’t join the band until September 25, 1990.

Two black-and-white photos of three young men with long hair sitting on a sloped concrete surface outdoors. The top image is a close-up; the bottom image shows them sitting apart with initials written on the concrete behind them.
jackshort67/Reddit

20. Robin Williams spent all day signing autographs at a homeless shelter in Boston in 1988

A man in a gray suit sits on outdoor steps, signing an autograph, while two casually dressed men with beards and plaid shirts sit on the steps behind him. A brick building and other people are visible in the background.
piefordays/Reddit

21. “This Rainbow Bright costume my mom hand-sewed for me in 1988.”

A young child in a colorful, padded costume with rainbow-striped sleeves, a red yarn wig, face paint, and holding a staff, standing indoors in front of wooden cabinets.
amaads/Reddit

22. Steve Carell as a brochure model in 1988

A man in a work uniform stands outdoors beside a yellow and red service truck, smiling next to hazardous waste reduction equipment and barrels. The text reads, Hazwaste Reduction and Removal Services.
IndoorBurrito/Reddit

23. Stan Lee with Hulk and Thor from the 1988 Hulk live-action TV show

Three men stand together: one dressed as a Viking-like warrior, one wearing sunglasses and a suit, and one painted green with muscular arms, resembling the Hulk, all smiling and clasping hands in front of control panels.
MathiasPrime/Reddit

24. An architect in his office in 1988

A man in an office sits at a desk using a vintage computer and keyboard. A large HP plotter printer is printing architectural blueprints. A framed artwork hangs on the wall behind him.
JohnApples1988/Reddit

25. Conan O’Brien and Bob Odenkirk in the SNL writer’s room in 1988

Two men are in an office. One is sitting and playing an acoustic guitar while the other, wearing glasses and a striped shirt, stands nearby watching. There’s a corkboard with papers and a photo on the wall behind them.
act1989/Reddit

26. Nick Offerman’s senior class photo from 1988. He was not only the president of the senior class, but he was also the president of the drama club, a saxophonist in the jazz band, and voted “Most likely to host the David Letterman Show.”

A hand holding a portrait photo of a young man in a suit and tie, smiling at the camera. The name “Nicholas ’88” is written in cursive in the lower right corner of the photograph.
BDWG4EVA/Reddit

27. The 1988 People Magazine photo shoot that united all the slasher movie icons

Four people dressed as iconic horror movie villains—Leatherface, Freddy Krueger, Jason Voorhees, and Michael Myers—sit and stand menacingly around a table with Halloween decorations in a dark, eerie setting.
People Magazine/NinjaDiscoJeans/Reddit

28. “My mom is coming to see me during her lunch break for my kindergarten graduation in 1988.”

A young boy in a graduation cap, yellow shirt, and red suspenders holds yellow balloons and a certificate while standing next to a smiling woman in a pink suit and glasses indoors.
SarcasticGamer/Reddit

29. Macy’s Thanksgiving Day Parade, New York City, 1988. Photo by Elliott Erwitt.

Two people sit by a large window as a giant Snoopy balloon floats outside, filling most of the view. City buildings and trees are visible in the background, and sunlight streams into the room.
Elliot Erwitt/Tony_Tanna78/Reddit

30. “My friend and I heading out to cruise the town in 1988.”

Two young people with hats pose with a black car featuring pink accents and a Metallica license plate. One sits in the drivers seat, while the other leans on the hood. Trees with autumn leaves are in the background.
userdeleted/Reddit

31. “Me and my 8th birthday, that was held at the local Burger King in 1988.”

A young boy with blonde hair sits alone at a table in a fast food restaurant, eating a meal with drinks and food wrappers in front of him. He wears blue shorts, a white shirt, and knee-high socks with stripes.
_metamax_/Reddit

32. “My mom was a punk in high school in 1988.”

Four young people stand in front of a Health Occupations Students of America sign, holding trophies. Three are smiling; one with a mohawk and leather jacket has a neutral expression. The photo appears old and worn.
RedditUser28947/Reddit

33. Mister Rogers throwing the opening pitch at a 1988 Pirates vs. Phillies game

An older man wearing glasses, a tie, and a dark cardigan holds up a baseball in one hand, standing and facing the camera with a slight smile in a black-and-white photo.
NomadSound/Reddit

34. Alyssa Milano and Christina Applegate in 1988

Two young women stand close together outdoors. One wears a gray tank top and ripped white jeans, the other wears a pink Grateful Dead t-shirt and holds what appears to be a concert ticket. Both look at the camera and smile slightly.
Hellvis_50s/Reddit

35. “My brother and his Pro Am II in 1988

A shirtless man wearing sunglasses and jeans stands in front of a red and white sports car with an open door, outdoors on a sunny day with trees and a wooden fence in the background.
userdeleted/Reddit

36. “My mom and her brand new boom box in 1988.”

A smiling woman in a colorful striped sweater holds a large vintage boombox on her shoulder, sitting indoors on a patterned chair with plants in the background.
bogjumly/Reddit

37. Russians eat American-style pizza for the first time from a food truck in Moscow, 1988

Three people eat pizza and drink soda in front of a food truck labeled First American Pizza in Moscow near Saint Basil’s Cathedral, with the cathedral’s colorful domes visible in the background.
marty_eraser/Reddit

Want more ’80s vibes after these vintage photos from 1988?

Dive into our arcade time capsule in 27 Vintage Photos of 1980s Arcades That Will Take You Back, revisit golden-era fast-food memories in 25 Vintage Photos of What Life Looked Like in 1980, soak up retro dine-in energy with 15 Nostalgic Photos To Remember When Pizza Hut Had Atmosphere.

'80s37 Vintage Photos From 1988 That Are Like a Time Machine
Colby Droscher
Colby Droscher
Colby has been in digital publishing for 15+ years. In a past life he was the Editor in Chief of Literally Media Entertainment brands (cracked.com, ebaumsworld.com, cheezburger.com).

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