Throwback Ads: 22 Bold and Quirky Billboards From Another Era

A vintage billboard advertises Nabisco Oreo cookies, showing two girls eating Oreos and a hand reaching for an Oreo from a TV screen. The sign reads “Switch to OREO.” Classic cars are parked below.

Before smartphones and digital ads took up all of our attention, billboards served as larger-than-life works of art that loomed over highways and city streets. Selling everything from cars and movies to rock ‘n’ roll and roadside diners, these (mostly) hand-painted signs were designed to catch your eye on the go. Whether it was a trippy-looking promo for a ‘60s band or a kitschy motel promise of “color TV and air conditioning,” billboards didn’t just sell things; they told stories.

Take a look at these 22 vintage billboards from the past that illustrate the significant changes in advertising over the years.

1. ‘Billboard for Big Bear Supermarket in Columbus, Ohio’ (1958)

A brightly lit vintage sign features a smiling woman with a grocery cart full of items, large red letters reading "BIG BEAR," and the slogan "Shopping pleasure... and courtesy await you!" at night.
morganmonroe81/Reddit.com

2. An Anti-Tobacco Billboard Seen Outside Zion, Illinois (1921)

A woman stands next to a large sign warning against tobacco use, calling it filthy and dangerous, and urging people to quit. Trees and a building are visible in the background. The photo appears to be from the early 20th century.
UserDeleted/Reddit.com

3. The Doors Promoting Their First Album in Los Angeles (1967)

Four men stand in front of a large billboard promoting The Doors' album, featuring the band’s name in a bold, stylized font and the slogan, "Break on through with an electrifying album.
CosmicAdmiral/Reddit.com

4. A Roadside Billboard Inviting Drivers to ‘Take a Sundae Drive’ to Farrell’s, Known for Its Old-Timey Charm and Giant Desserts

A colorful billboard advertises Farrell’s, showing a smiling server holding a large ice cream sundae. The sign reads, “Take a SUNDAE drive to FARRELL’S Fountain • Food • Fun.” Vintage cars are visible below.
AxlCobainVedder/Reddit.com

5. A Weathered (and Ultra Creepy) McDonald’s Billboard Advertising Burgers and a Playground Park for Less Than a Buck (1980s)

A faded McDonald's billboard advertises hamburgers for 59¢ and cheeseburgers for 69¢ plus tax, features Ronald McDonald, the Golden Arches, two cartoon children, and the slogan "Just A Smile Away.
SignificanceFun265/Reddit.com

6. Tourists Billboards Along Route 66 (1951)

A collage of five vintage roadside signs advertising attractions, including a 150 lb. canary, a man-killing boa constrictor, a 48 ft. prehistoric reptile, wildcats, and the El Morro cliff dwelling entrance.
UserDeleted / Reddit.com

7. A Pre-Opening Billboard for the Luxor Hotel and Casino in Las Vegas Advertising Its Debut (1990s)

A billboard announces "COMING... OCTOBER 1993" for Luxor Hotel and Casino, with gold text and pyramid logo. Below, it reads "Another Circus Circus Enterprise" against a blue background.
anon37391619/Reddit.com

8. A Ford Billboard for the 1955 Ford V8, Featuring a Two-Tone Sedan and Classic Mid-Century Styling in Front of a Dealership Lot (1950s)

A black vintage car is parked in front of a large billboard advertising a new Ford V8 car for 1955. The billboard features an illustration of a green and white Ford car with bold "FORD" lettering above it.
Cartonk/Reddit.com

9. ‘My Grandfather, W.S. Stuckey, In Front of a Billboard Advertising Stuckey’s Pecan Log Rolls’ (Early 1960s)

A man in a suit stands in tall grass in front of a large roadside sign that reads “1st Place Winner Pecan Rolls National Candy Award Stuckey’s.” The sign is positioned next to a highway.
StuckeysPecans/Reddit.com

10. A Chrysler Billboard Featuring a Flashy Model With Tailfins and a Smiling Couple Going for a Drive (Late-1950s)

A vintage billboard advertises a Chrysler car with a smiling man and woman inside. The word "CHRYSLER" appears in large letters, and "EXCITING!" is written in bold white text on a bright red background.
Cartonk/Reddit.com

11. Classic Americana: A Holiday Inn Motel Sign Inviting Travelers To Enjoy a Luncheon Buffet During the Week

A large retro Holiday Inn sign with a yellow, green, and orange color scheme stands by a road. The marquee below advertises a luncheon buffet. A church steeple and trees are visible in the background under a blue sky.
xologo/Reddit.com

12. ‘Children Looking at a Circus Billboard’ (1930s)

Four children stand in front of colorful old circus posters featuring lions, tigers, and performers, pasted on a wooden wall outdoors. One child is pointing at the posters while others look on with curiosity.
skipperbob/Reddit.com

13. A Massive Billboard Promoting ‘Batman Returns’ in New York City’s Times Square (1992)

A large "Batman Returns" movie billboard featuring Penguin, Batman, and Catwoman overlooks a busy city street with yellow taxis, pedestrians, and the Embassy Suites hotel.
moonandstars1984/Reddit.com

14. ABBA Poses in Front of Their Own Billboard in Los Angeles (1978)

Four people in colorful 1970s outfits pose smiling on a city sidewalk under a large ABBA billboard promoting the band. Buildings and street signs are visible in the background.
AxlCobainVedder/Reddit.com

15. A Young Woman’s Likeness Is Hand-Painted on a Billboard Above Manhattan (1947)

Three workers stand on a suspended scaffold high above a busy city street, painting a building’s exterior. Skyscrapers, billboards, and crowds are visible below. One woman stands confidently, hands on hips, looking outward.
FNaXQ/Reddit.com

16. Movie Posters for ‘Chatterbox’ and ‘Love Before Breakfast’ Plastered on a Brick Wall Between Houses in Atlanta, Georgia (1936)

Two old, weathered wooden houses stand side by side, with vintage movie posters pasted on the brick wall in front. The posters feature film titles and black-and-white images of actors. The scene appears quiet and deserted.
MyIpodStillWorks/Reddit.com

17. ‘Star Wars Billboard in Tokyo’ (1978)

A large, illuminated "Star Wars" movie billboard with Japanese text dominates a busy urban street scene at night, surrounded by colorful neon signs and buildings.
MidoriTea/Reddit.com

18. ‘A Coca-Cola Billboard on the Outskirts of Bangkok’ (1950)

Four children wearing hats and carrying baskets stand under a large Coca-Cola advertisement and a "Welcome to Bangkok" sign in an open, grassy area. The scene appears to be from a past era.
JumpySignature5588/Reddit.com

19. A Retro Billboard for Pontiac’s All-New Firebird Formula 400 (1970)

A billboard advertises the Pontiac Firebird Formula 400, featuring an image of the blue car. The text reads: "Pontiac's all-new Firebird Formula 400. The beginning of tomorrow.
Cartonk/Reddit.com

20. A Billboard for Purity Dairy in Nashville, Tennessee, Featuring Ernest P. Worrell and His Famous Line, ‘Know What I Mean, Vern?’

A billboard advertises Purity Dairy's 100th anniversary with a smiling man holding a milk carton. Text reads “Nashville’s Hometown Dairy for 100 Years! Know what I mean, Vern?” and features a blue “100 Years” badge.
JVstuff/Reddit.com

21. A Billboard for the 1968 Dodge Charger Promising ‘Dodge Fever’ With Just One Look (1968)

A black and white photo of a billboard featuring a 1968 Dodge Charger with the text: "'68 CHARGER One look and you've got Dodge fever." The billboard is in front of a brick building.
Cartonk/Reddit.com

22. A Playful Billboard for the Space Needle in Seattle, Washington. Certainly Not for Those With a Fear of Heights (1970s)

A billboard with the text "Get high with us." next to a colorful illustration of the Space Needle and the words "The Space Needle" in yellow bubble letters above it. Trees and a clear blue sky are in the background.
shelvesofmatterhorn/Reddit.com

More vintage ads:

On the left, a vintage Navy recruiting poster features a woman in a sailor uniform. On the right, a 1924 Jell-O advertisement shows a girl in a blue dress holding a tray, with bold yellow and white text.
LookWutIFound / fondlemeLeroy via Reddit.com
Author
Alina Wang

From Queens, New York, Alina has a Bachelors degree in Corporate Communications from CUNY Baruch and enjoys writing and creating content on a variety of topics, including lifestyle, politics, and, of course, wealth trends. Find her on X @atlasseventeen