14 Vintage Ads That Tried Way Too Hard to Be Funny
This list rounds up 14 vintage ads that tried to be funny but ended up being awkward, strange, or downright uncomfortable.
- Daisy Montero
- 4 min read
Some old ads tried to use humor to sell everything from soda to cigarettes, but the jokes often fell flat. These 14 vintage ads were meant to be funny, though now they come off as odd or even cringeworthy. They reveal just how much humor and advertising have changed over time.
1. Baby’s First Soda
krishna Kids Photography on Wikimedia Commons
This 1950s ad proudly proclaims, “This young man is 11 months old, and he isn’t our youngest customer by any means,” showcasing a baby enjoying a 7-Up. The attempt at humor falls flat today, highlighting a time when health concerns were overlooked for the sake of a catchy line.
2. Driving Miss Stereotype
Andrew Bone from Weymouth, England on Wikimedia Commons
A 1960s Mini Cooper ad depicts a woman looking terrified behind the wheel, suggesting that the car is so easy to drive, even a woman can handle it. The sexist undertone was likely intended as humor but now serves as a glaring example of outdated gender norms.
3. Fight Club: Cigarette Edition
Kky on Wikimedia Commons
Tareyton’s slogan, “Us Tareyton smokers would rather fight than switch!” accompanied by images of people with black eyes, was an attempt at showcasing brand loyalty. The humor is questionable, and the imagery unsettling, making it a memorable misfire.
4. Cooking Up Compliments
krishna Kids Photography on Wikimedia Commons
An ad proclaims, “So the harder a wife works, the cuter she looks!” attempting to humorously link domestic chores with attractiveness. Today, it serves as a cringeworthy reminder of past societal expectations placed on women.
5. Grammar Goes Up in Smoke
Timo Stein - Wampenseppl on Wikimedia Commons
Winston’s slogan, “Winston tastes good like a cigarette should,” intentionally used incorrect grammar for a catchy jingle. While it may have been memorable, the humor derived from grammatical errors doesn’t quite hold up.
6. The Family Tonic
Pabst Brewing Company on Wikimedia Commons
An old Rainier beer ad claims it’s “beneficial to young and old,” showing a child and an elderly man enjoying a brew. The attempt at humor by promoting beer as a health drink is both baffling and concerning.
7. Crash Course in Sexism
Filip Frid on Wikimedia Commons
A Volkswagen ad shows a car crash with the caption, “Women are soft and gentle, but they hit things.” The attempt at humor through gender stereotypes falls flat and is now seen as blatantly offensive.
8. Under Her Foot
Unknown author on Wikimedia Commons
Weyenberg’s shoe ad suggests keeping women “where they belong” — underfoot. The attempt at humor through dominance is now recognized as a glaring example of past misogyny.
9. Where’s Herb?
Burger King Corporation on Wikimedia Commons
Burger King’s “Where’s Herb?” campaign attempted to create a humorous mystery around a man who’d never eaten a Whopper. The confusing promotion left customers baffled rather than amused.
10. Blind Leading the Blind
Zahra Ibrahem on Wikimedia Commons
Apple’s “Lemmings” ad depicted blindfolded office workers walking off a cliff, aiming for dark humor. Instead, it was perceived as insulting, making it one of Apple’s rare advertising missteps.
11. Coffee Confusion
Maxwell House on Wikimedia Commons
Maxwell House’s ad featuring a man telling “Tiny” that “Coffee is like a friend” attempts to be endearing. However, the bizarre dialogue and context leave modern audiences more puzzled than amused.
12. Shaving the Baby
Garver at de.wikipedia on WIkimedia Commons
A Gillette ad featured a baby holding a razor, accompanied by the tagline, “Begin early, shave yourself.” The attempt at humor through exaggeration is clear, but pairing a razor with a baby feels wildly irresponsible today. What was once seen as playful now looks more like a safety PSA waiting to happen.
13. Drunk Babies and Daddy’s Beer
Otto Yamamoto on Pexels
A vintage Rheingold Beer ad showed a toddler reaching for a bottle while the father looks on, smiling. It was supposed to be lighthearted, as if the baby wanted a sip too. Today, it feels more like a red flag than a joke.
14. You Mean a Woman Can Open It?
Alcoa Aluminum on Wikimedia Commons
This vintage ad for Alcoa aluminum cans acted shocked that a woman could manage to open one on her own. The fake surprise was meant to be funny, but it aged terribly. What they saw as playful now reads like a slap in the face.