27 Awkwardly Funny Family Photos ~ Weird, Wacky and Wonderful

Enjoy a heartfelt perusal through another memory-filled album of hilarious and strangely familiar awkward family photos. From vintage photos to recent snaps, this collection of family pics is sure to resemble your family tree somewhere down the line.

Smile! It’s Weird & Funny Family Photos Time!

 

Caitlyn was never one to take her eye from the prize.

Caitlyn was never one to take her eye from the prize... ~ funny awkward family pics

 

Every Sunday, Minerva donned her best church hat and took down the devil with her icy stare.
Every Sunday, Minerva donned her best church hat and took down the devil with her icy stare. ~.~~.~ funny awkward family vintage photos, church clothes, hat

 

“Hurry’up, Randy. Walmart closes in 20 and we’re outta Luckies!
"Hurry'up, Randy. Walmart closes in 20 and we're outta Luckies! ~.~ funny awkward photos family

 

When Jackie mentioned role-playing, I never pictured this…
When Jackie mentioned role-playing, I never pictured this... ~.~ funny awkward family vintage pics portrait woman horse costume

 

The moment Def Leppard took the stage at Moondance Jam Classic Rock Fest.
The moment Def Leppard took the stage at Moondance Jam Classic Rock Fest. ~.~ funny awkward family pics fat man dancing at concert

 

Another crazy Saturday night at Aunt Dorothy’s.
Another crazy Saturday night at Aunt Dorothy's. ~.~ funny awkward family vintage photos

 

As usual, Harold was the sole attendee at the annual Hedonistic Weekend at Wamplers Lake.
As usual, Harold was the sole attendee at the annual Hedonistic Weekend at Wamplers Lake. ~.~ funny awkward family vintage photos, naked grandpa picnic table

 

My, how quickly radiation can affect a little boy.
My, how quickly radiation can affect a little boy. ~.~.~ funny awkward family vintage photos 1950s 1960s mom boy posing nuclear bomb test

 

Millie was always first to volunteer for guard duty at Shady Acres Nursing Home.
Millie was always first to volunteer for guard duty at Shady Acres Nursing Home. ~.~ ~.~ funny awkward family vintage photos

 

Amanda finally found an accepting audience for free form acid jazz.
Amanda finally found an accepting audience for free form acid jazz. ~.~ ffunny awkward family vintage photos

 

Prepubescent Suburban Gangstas on Red Bull.
Prepubescent Suburban Gangstas on Red Bull ~.~ ~.~ funny awkward family vintage photos

 

All the housewives of Chesterfield County love Butcher Bob’s meat.

All the housewives of Chesterfield County love Butcher Bob's meat. ... ~.~ funny awkward family vintage photos

Kevin… Outta gas but full of class.
Kevin... Outta gas but full of class. ~.~ funny awkward family vintage photos, shirtless boy in high heels

 

Janice, still fabulous after all these years.
Janice, still fabulous after all these years. ~.~ funny awkward family photos, vintage pics, 1960s fashions 1970s

 

Hair and teeth, the defining qualities of the Winfree children.
Hair and teeth, the defining qualities of the Winfree children. ~.~ funny awkward family portraits, vintage pics

 

That baby just saw some shit
That baby just saw some shit. ~.~ funny awkward family pics, vintage photos portrait of kids

 

The Many Sides of Martha.
The Many Sides of Martha. ~.~ funny awkward family vintage photos

 

Frank and Nellie’s annual vacation got off to a booming start.
Frank and Nellie's annual vacation got off to a booming start. ~.~funny awkward family vintage photos, car accident, roll over man woman posing with wrecked car gasoline leaking

 

You can bluff but never bullshit Gladys.
You can bluff never bullshit Gladys ... ~.~ funny awkward family vintage photoss grumpy old woman playing bridge

 

Why you never ride to the Sears Portrait Studio with the car windows down.
Why you never ride to the Sears Portrait Studio with the car windows down. ~.~ funny awkward family vintage photos, 1980s hair, portrait, sisters, fashion

 

You… me… and S.W.A.T. team makes three.
You... me... and S.W.A.T. agent makes three. ~.~ funny awkward family vintage photos

 

Few knew that Grandma was a ripper.
Few knew that Grandma was a ripper. ~.~ funny awkward family vintage photos. granny skateboarder

 

The day a ’72 Ford Pinto Changed Gerri’s life forever.
The day a ’72 Ford Pinto Changed Gerri’s life forever. ~.~funny awkward family vintage photos, 1970 game show, woman big hair, fashions

 

That awkward moment when you wake up in the middle of the night and realize your pictures are ready.
That awkward moment when you wake up in the middle of the night and realize your pictures are ready... ~.~ funny awkward family vintage photos, woman Walmart wrapped in bedsheet

 

Why the Franklin kids never showed their faces in public.
Why the Franklin kids never showed their faces in public. ~.~ funny awkward family vintage photos, husband wife ice skaters skating pairs, 1970s

 

‘Til this day, Vito’s mother never let anyone one pick on her little boy.
'Til this day, Vito's mother never let anyone one pick on her little boy. ~.~ funny awkward family vintage photos Italian mom gangster

 

When school schedules picture day and pizza day on the same day.

When school schedules picture day and pizza day on the same day. ~.~ funny awkward family photos

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