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Classic Captions Contest – 1956 Cadillac Edition

Can you believe the last time we did a Classic Captions Contest here on Hooniverse was back in January of 2017? If you missed that run, travel back in time to this adventurous family, wearing matching khaki “outdoorsy” outfits posing in front of a rad 1987 Toyota Van. Clearly the father, Scott, is armed and ready to photograph the living daylights out of anything “nature” he sees with his green vest. For this revamp of our hilarious Classic Captions Contest, let’s step back even further to this brochure for Cadillac’s 1956 lineup.

It’s a shame that Cadillac today isn’t the Cadillac they used to be. They made cars that were dazzling and high-class. A sophisticated Detroit image you’d park in your driveway (backed in, of course), to show off to friends, family and the neighborhood that you’ve made it; you’ve accomplished something. Dig up any old sales brochure for Cadillac and you’ll see people dressed to the nines wearing white gloves, hats that belong on top of Frank Sinatra’s head, and pressed suits that almost matched their car’s leather-bathed interior.

Sure, today’s Cadillac still builds a fleet of quality, luxurious and even track-ready vehicles, but they all lack that proud, ambassador-esque flair that, say in this case, a 1956 Series 62 Coupe De Ville (pictured) had. You can’t help but see the image above, and then look at shots of the new XT4 crossover and feel depressed. The posh just isn’t there.

Analyze the advertisement above and write your own story for it. We see a swaggered-up couple walking towards a red Coupe De Ville, while behind them, a mysterious man in a black suit nervously holds what appears to be a styrofoam take-out box clutched tightly under his right arm. Our second mysterious thick-rimmed glasses man, on the right seems to be in-stroll and grasping a brown leather dossier with ____ inside.

You finish the rest. Let the comments section below be your script.

  • Alff

    Mr. Drysdale is feeling smug after having diversified into men’s hats, newspapers, exterior building tiles and whitewall tires. Truly a future-proof portfolio.

  • 0A5599

    Kitty had a little known story.

    Jack Ruby ensured it stayed that way.

  • GTXcellent

    “Mrs. Johnson…… Mrs. Johnson… MRS. JOHNSON PLEASE PAY ATTENTION. I repeat, I want you to walk forward 5 steps – on the yellow line. Again tell me, how many martinis did you have at lunch?”

    (side note – YEAH, Classic Captions is back again!)

  • P161911

    Frank was sure that his wife had spotted him with his secretary Penny.

  • P161911

    I hope you were joking about the Styrofoam takeout box. That’s a newspaper! I’m not that old.

    • I keep having to explain to curious grad students that those little pushbutton clamshell/trapdoor things built into the walls next to the elevator on each floor are ash trays left over from the days when people were allowed, indeed expected, to smoke indoors, so yes, we are that old. It doesn’t help that down the hallway is a small, empty recess formerly occupied by a pay phone. It really doesn’t help that I remember using that pay phone.

      • Alff

        I have a similar conversation with my daughter’s friends about the window cranks in my car. To date none have asked about the choke lever.

      • P161911

        Ideas:
        Tell them it cost $1 to ride the elevator. It is on the honor system. Deposit your money there. See how much you can collect in a week.

        Place your car keys in there for the valet to bring your car around.

        ???

        • I would mourn all of my wasted opportunities if I thought for a moment that our grad students had (1) money or (2) cars.

  • “Okay, they changed the grille slightly. Still no other major differences. Don’t worry about the grille. Don’t even look at it. Stick with the plan, Johnny. Keep what you’ve got and keep going. You can do this.”

    The years following 1954-56 would come to present more of a challenge for Mr. Cash.

  • Citric

    “Hello Mr. Gage, I’m your 4:00 indecent proposal.”

  • hwyengr

    Before the internet, mobile phones, and electronic payment processing, hailing an Uber was much more labor intensive.

  • I_Borgward

    Lenny the bag man was right on schedule, and started to cross the street. Floyd reached for the Racing Form with the microfiche tucked inside, ready for the hand off. But, Lenny being Lenny, he never passes up the opportunity to gawk at a passing dame. That’s all it took. In a split second, Spike mashed the gas on the Cad, and Lenny got up close and personal with Spike’s whitewalls. A coup de grâce with a Coupe de Ville.

  • Erik the Awul

    A little known story… about Cadillac’s first foray into autonomous driving. This is the last photo of Mr. Smith.

  • “Christ what an a**hole.”

  • Princess Grace finally gets her new Cadillac. “I was so tired of riding around Monaco in those stuffy old Rolls Royces.”

  • Batshitbox

    The 42nd attempt to get the shot captured yet another clueless old fart stepping in front of the damned car.

  • Luxury Lexus Land-yacht

    This prisoner exchange is not going as expected.

  • ConstantReader

    “I’m gonna take her for a ride. And I’m gonna take the Caddy.
    Just hand over that briefcase, Smedley, and nobody gets hurt!”

  • Yellow Urinalist

    “Now that Kennedy is out of the way & we have the committee in our pocket, lets party at Bartiloche !

  • Thanks for the Memories

    “Yah, Kissinger loaned us this one – says her name is Brice Taylor, Sydney Gotlieb says she has the latest MK Beta Kitten programming”