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Oh, how quickly things age poorly! From Microsoft's hilariously premature iPhone funeral to advertisements that would never make it past the first draft today, these photos remind us that history isn't always kind to our choices. Remember when newspapers thought nothing of listing now-disgraced figures as "bachelor of the month"? Or when special cups with mustache guards were all the rage for proper gentlemen?

These images capture moments, products, and ideas that seemed perfectly reasonable at the time, but now make us cringe, laugh, or simply wonder what on earth people were thinking. Some reveal outdated social attitudes, others showcase spectacular business miscalculations, and a few are just plain bizarre. Come take a walk through this photographic time capsule of decisions that didn't quite stand the test of time.

#1

Joan Trumpauer Mulholland Was Arrested For Protesting In 1961. She Was Tested For Mental Illness Because Law Enforcement Couldn’t Think Why A White Woman Would Want Civil Rights

Young woman in a vintage mugshot, reflecting a seemingly ridiculous moment from the past.

Jackson Mississippi Police/Sheriff's Department 1961 Report

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    #2

    A Cartoon About A Hypothetical "Pocket Telephone," From 1919

    Cartoon depicting ridiculous scenarios with early mobile phones, including running for a train and attending a concert.

    The British Library Board Report

    #3

    Arch Duke Ferdinand Of Austria, Posing As A Mummy, 1894

    Man's face humorously peeks through ancient Egyptian sarcophagus, looking ridiculous.

    AnonymousJoe12871245 Report

    James016
    Community Member
    8 months ago Created by potrace 1.15, written by Peter Selinger 2001-2017

    Mad lad just wants some peace and quiet.

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    #4

    We All Got Vaccines, Except Dad

    Family gathered around father in iron lung due to polio, highlighting importance of vaccination.

    Ebonystealth Report

    Petra Peitsch
    Community Member
    8 months ago Created by potrace 1.15, written by Peter Selinger 2001-2017

    Past repeating itself in the near future for some unfortunate fellow-humans.

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    #5

    Family Portrait During The Spanish Flu, 1918

    Vintage photo of a family wearing masks, including a cat, posing outdoors, capturing a positively ridiculous moment.

    Dublin Heritage Park and Museums Report

    Multa Nocte
    Community Member
    8 months ago Created by potrace 1.15, written by Peter Selinger 2001-2017

    Even the cat knew better than the freakish anti-maskers.

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    #6

    Reusable Shopping List From The 1920s

    Hand holding a vintage grocery list tracker with metal sliders, illustrating ridiculous past shopping tools.

    Just don't lose it.

    Larirari Report

    Multa Nocte
    Community Member
    8 months ago Created by potrace 1.15, written by Peter Selinger 2001-2017

    We had one of those, although it had different items listed.

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    #7

    In The Victorian Era, Men Used Special “Moustache Cups” To Protect Their ‘Staches While Drinking Hot Tea

    Vintage photo of surreal mustache cups with faces, illustrating ridiculous retro design.

    CharmaineZoe's Marvelous Melange Report

    Lee Gilliland
    Community Member
    Premium
    8 months ago Created by potrace 1.15, written by Peter Selinger 2001-2017

    The mustache wax would melt😂😂😂

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    #8

    Cigarette Holder For Nudists, 1938

    Man demonstrating a leg-strapped cigarette holder for nudists, highlighting a unique solution from a 20th-century publication.

    Popular Science Report

    Multa Nocte
    Community Member
    8 months ago Created by potrace 1.15, written by Peter Selinger 2001-2017

    This is delightful! I never would have stopped to consider the needs of the n**e. My eyes are opened (but not looking directly at you, mind you).

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    #9

    The Day My Kid Went Punk, Abc After-School Special (1987)

    Retro TV scene depicting a punk-themed family discussion, capturing a seemingly ridiculous moment.

    Sober in a Nightclub Report

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    #10

    Nice One Google

    Google in 1999, described as a pure search engine without ads or distractions, highlighting its simplicity.

    acidcow.com Report

    #11

    Actual World Trade Center Visitor Brochures From 1985

    Brochures with the Twin Towers and text, "The closest some of us will ever get to heaven," appear ridiculous now.

    Ned2350 Report

    #12

    Liberace Takes A Bubble Bath, 1978

    Man in ornate bathtub surrounded by luxurious decor, wearing rings and smiling, capturing a ridiculous moment in retro style.

    Glenn Kelman Report

    PunchinelloTX
    Community Member
    Premium
    8 months ago Created by potrace 1.15, written by Peter Selinger 2001-2017

    I had the pleasure of seeing a tremendous lot of things from his estate after he passed away (using BP phrasing). My friend, Yvette, was handling the sale of much of it, and she allowed me to wander alone and poke around to see what I might like to buy before it went public. Holy Moses! Gaudy, gilt, overdone, but oddly charming. He had a very special style which on close inspection was uniquely refined. I didn’t buy anything but now, many years later, I regret it. A man of unwavering talent and a strong sense of self despite many detractors. Rest in Plushness, Lee.

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    #13

    Housewife Poses With A Weeks’ Worth Of Groceries In 1947

    Woman with vintage groceries lined up, showcasing ridiculous items from the past.

    She Spent A Total Of $12.50 A Week (Not Including Milk) To Buy Her Groceries. On This Budget, She Is Able To Feed Herself, Her Husband, Her Four-Year-Old Twins And Her Cat.

    Crash Report

    Petra Peitsch
    Community Member
    8 months ago Created by potrace 1.15, written by Peter Selinger 2001-2017

    I don't know, what are wrapped in the front of the photo, but there are too much caned food for my taste, and just 3 pieces of fresh items. 3 very small pieces.

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    #14

    Flight Was Achieved Nine Days Later

    Newspaper headline from 1903 declaring flying machines won't exist for a million years, now seen as ridiculous.

    Chuffnell Report

    Petra Peitsch
    Community Member
    8 months ago Created by potrace 1.15, written by Peter Selinger 2001-2017

    Imagine the level of how stupid this guy felt himself .....

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    #15

    The Most Inappropriate Ad Of All Time. 1975

    Vintage ad for Love's Baby Soft perfume featuring a young woman with curly hair holding a teddy bear.

    Marcel Report

    #16

    My Dad Used To Cut His Shirts, He Said It Was Common For Men To Show Their Belly Buttons, 1980s

    Man with long hair wearing a cropped "Soccer Training" shirt and jeans indoors, capturing a ridiculous fashion moment.

    AndyWindir Report

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    #17

    This Ad In A 1968 Life Magazine

    Black-and-white ad with a man in a suit, eyes covered, featuring text about parental guidance on d***s.

    gonicskoller Report

    Multa Nocte
    Community Member
    8 months ago Created by potrace 1.15, written by Peter Selinger 2001-2017

    I looked and looked for someone like this back in the day and could never find him.

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    #18

    Helping The Less Fortunate, Huh?

    Man in apron talking jokingly in a room, with a humorous caption about helping, reflecting on ridiculous situations.

    CBS Report

    Multa Nocte
    Community Member
    8 months ago Created by potrace 1.15, written by Peter Selinger 2001-2017

    I can't even look at his nasty face without breaking into a rash.

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    #19

    Household Hint From An Old Magazine

    Hand holding a flashlight battery above a fireplace, illustrating ridiculous safety advice from the past.

    Pile Report

    Ace
    Community Member
    8 months ago Created by potrace 1.15, written by Peter Selinger 2001-2017

    With the batteries of that time this was not such a crazy idea as it might sound. There was no explosion risk as they were not sealed, the outer casings being made of cardboard, the component parts were not toxic when burned and the technology to recycle them did not exist.

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    #20

    Ah, Simpler Times

    Man by a sign banning airplane glue sales to minors; a ridiculous look back at past regulations.

    craigster59 Report

    Ace
    Community Member
    8 months ago Created by potrace 1.15, written by Peter Selinger 2001-2017

    That stuff, aka polystyrene cement, was brilliant.

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    #21

    1950s Valentine

    Vintage Valentine card with a skunk, red heart background, and a humorous message that seems ridiculous now.

    ebay Report

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    #22

    Hefty Girls Wanted For Police Force (Must Be Fairly Good Looking). London Metropolitan Police, 1930s

    Vintage advertisement humorously recruiting hefty women for police work with headline about career obstacles if married.

    random-person-42 Report

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    #23

    1975 Patons Knitting Pattern, For Larger Sized Woman

    Two women modeling yellow knit tops on the cover of a vintage "Big Sizes" knitting book, 1970s fashion.

    Ebonystealth Report

    #24

    Old Kitchen Appliance Ad

    Retro ad with a couple, promoting a kitchen mixer, highlighting outdated roles. Ridiculous looking back now.

    Pile Report

    CK
    Community Member
    8 months ago Created by potrace 1.15, written by Peter Selinger 2001-2017

    Is this supposed to imply that she's married to a kitchen appliance?

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    #25

    Microsoft Employees Holding A Funeral For The iPhone Following The "Success" Of Their Windows Phone

    People carrying a massive oversized smartphone into a hearse, looking back humorously in a surreal setting.

    Mehr News Report

    Petra Peitsch
    Community Member
    8 months ago Created by potrace 1.15, written by Peter Selinger 2001-2017

    To be fair that phone wasn't bad. They just forgot about the 1st marketing rule: Always target the youngest generation with your ads, what you are legally allowed.

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    #26

    Asparagus Group From Miss Gatchell's Pageant, Lee County Alabama, April 16, 1925

    Three people wearing ridiculous pencil costumes, holding hands in a grassy area.

    notbob1959 Report

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    #28

    Sorry Man

    Online comment from 2007 predicting issues with touchscreen phones; now seems ridiculous in hindsight.

    l-am-Not-Me Report

    CK
    Community Member
    8 months ago Created by potrace 1.15, written by Peter Selinger 2001-2017

    There are pretty major problems. I miss my keyboard phone so much!

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    #29

    My Great Aunt Had A Japanese Hunting License (She's Dead Now)

    Antique hunting license mocking wartime propaganda, featuring exaggerated and offensive imagery.

    veganssuckmyasshole Report

    CK
    Community Member
    8 months ago Created by potrace 1.15, written by Peter Selinger 2001-2017

    Racists are really bad at animal metaphors.

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    #30

    How I Lost My Husband... And Won Him Back Again!

    Vintage ad featuring a couple with the woman looking distressed and a Lysol bottle, highlighting feminine hygiene claims.

    Lisa Wade, PhD Report

    Multa Nocte
    Community Member
    8 months ago Created by potrace 1.15, written by Peter Selinger 2001-2017

    My eyes rolled back so far they actually came out of my head.

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