Last Weeks Ugly Brother Winner:

Wait'll we get our Hanes on you.

Boom - Unknown

Jessica's "Pimps" son!

Superdad22 - Fort Wayne, IN

Some people will go to any length trying to fit in.

Don

Can somebody adjust these new microphones for us?

Don

Acting out fantasies can spice up your sex life.

Don

Oh no! Another cheap imitation from Japan!

Chan W.

Jessica Simpson before she puts on her makeup.

Don

It looks like President Bush started doing cocaine again. And now he's a cross dresser too.

Don

It looks like President Bush started drinking again.

Don

Everybody and I mean everybody is buying the new weed trimmer from Black and Decker!

Chan W.

Simon says pretend you're Jessica Simpson!

Chan W.

You'd smile too if the real Jessica Simpson was your housewife.

Don

The other day, my friends and I went to this "Gentleman's Club". One of my buddies wanted to impress us so he pulls out a $10 and put it on the stripper's butt.Not to be out done, my other friend pulls out a $50 bill. He calls the girl back over, licks the $50, and puts it on her other cheek.Now the attention is focused on me. What could I do to top that? I got out my wallet, thought for a minute. Then the banker in me took over. I got out my ATM card, swiped it down her crack, grabbed the $60 bucks and went home.

Don (Joke, not a caption)

Finalists getting ready for the wet tee-shirt contest.

Don

A Rolling Stone clone!

Jerry Norbrook - NY, NY

The poster child for unisex underwear!

Jerry Norbrook - NY, NY

Men behaving badly!

Jerry Norbrook - NY, NY

Guys didn't mind "sucking up" to Jessica.

Don

Then why have a picture if you can post captions that make no sense?

Don

Broadway tryouts are always fun to watch!

Jerry Norbrook - NY, NY

Who can say if they are or if they are not? Let the Voters decide!

Answer to Don

Slick Willy "BJ" Clinton lost his hair and he put on a few pounds but he's still very skilled at dancing around the issues!

Xray - Amery, WI

Aren't these captions supposed to have something to do with the picture?

Question from Don

What do Ted Kennedy and OJ Simpson have in common? They both got away with MURDER.

Xray - Remember, Chapaquitic?

Dick Cheney's lesbian daughter Mary liked to pretend she was Jessica.

Don

Ted Kennedy's son likes to fly like an Angel, but he can never seem to find his LEFT WING.

Xray - Amery, WI

The new boy band backup group for Jessica.

Don

The only difference between Herb and Jessica is PhotoShop software! (It can make even Hillery look good!)... Ummm.... forget that last remark.

Xray - Amery, WI

No I am not gay..But the guy who talks on the one news show, I believe Good Morning America and helps people with remakes is a good looking sucker!

Diane - Spencer,WI

The disguise almost worked but he couldn't find high heels that fit him.

Don

The difference between gay people and Jessica..There fun to talk to,their not fake,they dress better and they are smarter and always just fun to be with and we make it on news shows all the time,doing fun stuff people really like.

Diane - Spencer,WI

People always got Jessica and Jessie mixed up.

Don

Jessica has a stand-in for everything.

Don

The cleanup crew had more fun after Jessica's concerts than during them.

Don

Jessica's smart little mouth is all daddies money,but if they put her in a real barn and told her to scoop horse dung,she probably wouldn't know what a pitch fork was used for.

Diane - Spencer,WI

Everyone knows the old story: He was a loudmouthed, gay bashing, Christian in public but he danced around in pink underwear in private.

Don

Herb in his underwear: $12.00, Jessica Simpson in her underwear: $1,143.00, Hillery Rotten Clinton in her underwear: Priceless!

Xray - Amery, WI

I'm sweet and what a sin!

Diane - Spencer,WI

I don't only vacume like Jessica, I rock like her too!

Diane - Spencer,WI

Yep! Us people from WI really know our cheese and cheese-y people go places.

Diane - Spencer,WI

Someone gave Herb a poster of Jessica Simpson, but he admits that he prefers HOMER Simpson!

Xray - Amery, WI

A fake smile and hair color and a fixed up body... Who knows what she's done to look that way...! At least I am real!

Diane - Spencer,WI

Diane's captions are just as cheesy as Xray's because they are both from WISCONSIN!

Xray - Amery, WI

She's got the money and the looks,but I have my pride!

Diane - Spencer,WI

Hey Jessica! You think your good. Well!Look and weep!Sweet Heart!

Diane - Spencer,WI

Every man has a girl, hiding in their sole!

Diane - Spencer,WI

Mr. Clean's son is an embarrassment to his father.

Xray - Amery, Wi

Poor SuperBob failed to take SuperWingman's sage advice and is now forced to wear superthick glasses -- which explains why he looks like he got dressed in the dark, but doesn't explain why he became light in the loafers.

SuperBoom - Up, up and away

SuperBoom wisely refuses to use her X-ray vision to look at Gray's Anatomy.

David Winger - Woodland Hills, CA (Calling it a CripticNight...till tomorrow)

Boomsicle and Wing-a-ding know everybody loves a good puck.

Bubba-boom!

FINALLY and utterly forgetably...Other little known facts about Boomer Esiason courtesy of the Boom-Wing Archives of Useless Sports Trivia. He liked to be in control with good field 'position'. He loved to watch punts that were well hung. He kept the pigskin in the pocket. And he always kept in shape by managing his biological game clock!

David Winger - Woodland Hills, CA

Boomsica Pimpson and The Wingman take a breather from their weekend housecleaning to "sher" a laugh with the very punny Bubbles "Bubz" LeRoy -- who certainly knows old dirt bags when she sees them.

On behalf of Booms, Bubz, and The Wingman - Temporarily All Boomed Out

Former Cincinnati Bengals QB Boomer Esiason (pictured here tidying up the broadcast booth where he now works) admits he spent too much time staring at the tight ends and wide receivers in front of him when he should have put his backfield in motion and let the burly men behind him score.

Old Old Boom Boom - Trading sports memorabilia with The Old Wingman

New Fall television show--"Pimp My Carpet!"

msquanna - Larry's clean & sober! Congrats

Miss America's drinking problem...only the tip of the iceberg!

David Winger - Woodland Hills, CA

Say Boomer: the sadest thing about us knowing all these facts about Boom Boom Geoffrion... We're really showing our age!

David Winger - Woodland Hills, CA

Wow! The Boom knows her hockey! Boom Boom Geoffrion was indeed sent to the eternal penalty box in 2006. As a fellow Winger I should have known that. Other facts about Boom Boom: On and off the ice he was a notorious hooker. Rumors have been resurfacing about a suspected affair with a Zamboni machine. He relished receiving major penalties for body checking, butt-ending and handling an illegal sized stick. His favorite teammate, of course,...the 'Pocket Rocket' Richard.

David Winger - Woodland Hills, CA

Boomsica Pimpsom and Wingman clean up their acts.

Bubz

Hockey Hall of Famer Boom Boom Geoffrion (pictured here tidying up the Canadians' locker room) did everything for his teammates. He would spend hours checking out their equipment or showing them how he handled his stick. He'd gladly get down on his hands and knees searching for a good puck while explaining what a hat trick really meant. Recently he spent time confessing his personal hockey secrets to a fellow Wingman, in hopes of creating future scoring opportunities. But perhaps his greatest feat was learning to speak from the grave after passing away on March 11th of 2006.

Booming Back - Banging on the glass

Wildon applied for a job as the Fox News Channel Anchor. Unfortunately for him, he is neither fair nor balanced!

Xray - Amery, WI

Even more astonishing facts from the desk of the Wingman: Boom Boom Geoffrion (pictured above) who played hockey for 14 seasons with the Montreal Canadians now admits to the following: 1) He didn't mind all that holding, clutching, and grabbing. 2) Loved those slap shots. 3) Thought Stanley's Cup was undersized and, oh yes... didn't miss a period in his 14 years.

David Winger - Woodland Hills, CA

More astonishing facts from the desk of the Wingman: Boomer Esiason (pictured above) played football for ten years with the Cincinnati Bengals...and NEVER missed a period!

David Winger - Woodland Hills, CA

One of George Dumbya Bush's twin daughters hallucinates after getting into her father's coke.

Booming Away - Feeling sorry for a pathetic man

Happy Feet.

Boomguin - The frozen tundra

One thing that Gary could do that Jessica couldn't...a Peterbilt commercial!

David Winger - Woodland Hills, CA

After more than 34 years of trying, Herb still wants his face on Gerber baby food jars.

Xray - Amery, WI

Both the floor and Gary were badly in need of a waxing.

David Winger - Woodland Hills, CA

Why Boomer Esiason could never complete a pass!

David Winger - Woodland Hills, CA

Herb realized that he desperately needed glasses when he mistook Jessica Simpson for Hillary Rotten Clinton!

Xray - Amery, WI

The Wingman struts his stuff wearing only his Fruit of the Booms.

The Boom Box LOL - Dancing to the music

Gary was missing one thing...a boom box!

David Winger - Woodland HIlls, CA

Just thank goodness he's not imitating Britney Spears.

David Winger - Woodland HIlls, CA

Bob auditions for "Gay, Straight or Taken".

The Boom Tube - Confusing people

Herb is hoping he could date Jessica because he likes the way she handles a SWIFFER!

Xray - Amery, WI

Herb makes fun of Jessica because he's secretly in love with Peggy!

Xray - Amery, WI

Frank, the Prince of Monaco, demonstrates how he sweeps both women and men off their feet.

The Electric Boom - Tidying up

Herb wanted to get a $500.00 makeover so that he could compete with Jessica. He was bummmed out when they told him the cost would be $500 MILLION with no guarantees!

Xray - Amery, WI

Another example of a real loser imitating the actions of person they secretly admire.

Tra La La Boom - Bringin' it without sucking up to anyone

Jessica Simpson.... The QUICKER PICKER-UPPER!

Xray - Dennis,Your Super Pole cap is hilarious!

After dreaming about Jessica, Herb cleaned his house. He also had to clean his underwear!

Xray - Dennis.... Your

Victoria's Real Secret

David Winger - Woodland Hills, CA

Molly Maid is now Pauly Maid.

David Winger - Woodland Hills, CA

Bob was never the same after hearing the draft might be reinstated.

Corporal Boom Klinger - The 4077 M.A.S.H. unit

Broom Broom LaRue. (Of course lew's poster reference in the LOL BoomHilda caption is actually the 100% accurate one. Ahem.)

Boom Boom LaRue - It begged to be said

Meet Jessica Kim-sun.

Amy

I put the same picture on my wall at home in hopes it would influence my wife to vacuum. I soon found myself in a very clean environment, but then the hospitals are ALWAYS clean.

Dennis Silver - Asheville, NC

I can't remember if my friend said he's coming over tomorrow for a 'Super Hole' or a 'Super Pole' party. Either way I don't want the house to be dirty.

Dennis Silver - Asheville, NC

SO!...After twenty million dollars of government research money, we can safely say that giving men Estrogen does NOT help them loose weight.

Dennis Silver - Asheville, NC

Herb danced around the room with his Swiffer Mop when he found out that Congress will soon raise the Minimum Wage. He thinks he can now afford to date Jessica!

Xray - Amery, WI

Wildon keeps his cellphone tucked away in his undies because he just loves the vibration when people call! The only problem is.... NO ONE EVER CALLS HIM!

Xray - Amery, WI

Steroids can have unwanted side effects on your body.

Don

jessica simpson meets mr. clean meets randy jackson meets jackie chan... he'll pose for you, i guess it DEPENDS!!!!!!!!!

enron - toledho

Amy delights in the fact that one size fits all.

wildon

What happens in Vegas, stays in Vegas.

Don

Tyra, who said you gained 40lbs. I think you look great!!! but where is your wig??

sally lou - ohio

Uncle John in his brand new X-mas boxers!!! nice fit...

aaron - toled-ho

Definition of SUPER BOWL: Two large scoops of Spumoni in a bowl.

Xray - YUMMY!

Rodny shows off his new invention -- an electronic Hockey Stick. He says when you're not playing Hockey, you can actually use it to mop your kitchen floor! That's BRILLIANT, RODNY!

Xray - Amery, WI

There once lived a man named Fred, who was big and so very well fed. He posed in the nude, got brutally sued, now his fame has gone to his head!

Xray - Amery, WI

"A real mans wife of the year, ow ow!!"

sally lou - toledo

Bubba had a hard time adjusting after being released from prison.

lew

Another Joe Namath wannabe posing for a women's underwear ad.

Xray - Amery, WI

Double your pleasure with Doublemint gum.

Coyote Killer - Mojave, Ca.

"I can bring home the bacon, fry it up in the pan, and never let you forget you're a man."

Coyote Killer - Mojave, Ca.

"Do these pink panties make me look fat?"

Coyote Killer - Mojave, Ca.

"Oh George, you really do suck."

Coyote Killer - Mojave, Ca.

There's a little difference in their appearance, but their IQ is the SAME.

Dennis Silver - Asheville, NC

Clems next dream is to become a Dust Bunny.

lew

The secret to success is obviously in the grip.

lew

Boris is making an ernest effort to diet...he doesn't want to be a 'transfatual' all his life!

David Winger - Woodland Hills, CA

Mortimer's fantasies often required a bit of cleaning up.

lew

Boom-Hilda enters the modern age.

lew - The image on the poster of course :)

This obviously destroys the parrallel universe theory.

lew

Women loved Bob cuz he had a long hard stick and really knew how to handle it.

Ms. Boom - Yes, Wingman, tis true. I am woman, hear me boom

No, Boomer, I would have never expected that of you...you can actually vacuum!

David Winger - Woodland Hills, CA

J. Edgar Hoover's grandson carries on a family tradition.

Boomvestite - Investigating the F.B.I.

Don't ask, don't tell.

Boom all that you can boom - Confined to barracks

Jessica finally tells her story in Rolling Stone Magazine titled, "My Ugly Brother".

Xray - Amery, WI

It's true. Prison changes a man.

Boom 002117895 - Wingman...there's something you should know about me

Morris purchases all his clothes at the Gender GAP.

David Winger - Woodland Hills, CA

What guys like Wildon, X-Ray, Frank, David, The Boomer and Dennis really didn't want to see: Bruno, the 'Poster Woman' for phone sex!

David Winger - Woodland Hills, CA

Beauty and the beast.

P.R. - Smalltown, USA

Carefree and hair-free.(Nice win, Larry!)

P.R. - Smalltown, USA

Twins don't always look alike!

Chan W.

Marvin was just cloning around.

David Winger - Woodland Hills, CA

Dancing With The Stars IV!

Chan W.

Jessica's and Nick's son really took after his mother.

Don

"I gained 85 pounds, lost my hair, and had to get glasses thanks to Jenny Craig. You can too."

Don

Chris lost the modeling job after she/he had the sex change operation.

Larry Fishbach - Aurora, OH

Sorry, Herb, but SHAPE means everything!

Xray - Amery, WI

Herb wants to make his spouse jealous, but Harvey isn't bothered by it.

Xray - Amery, WI

Meet the newest member of the Simpson family. Homely Simpson!

Chan W.

Who says we Asians can't dance!

Chan W.

Doesn't Peggy look GREAT! (Um... I'm talking about the picture on the wall in case your were confused)

Xray - Amery, WI

Your next American Idol.

Boomon Cowell - Using blunt force

Frank secretly tried to model himself after celebrities.

The Infamous Boom - Hiding behind shades

Nick's replacement for Jessica really sucked.

Boommaker - Bringing people together. By force if necessary.

"Well, I WAS a bit younger there!"

Frank Monaco - Coconut Creek, FL.

Herb works a a model, hoping that one day he can afford an extension cord for his Swiffer so that he could do some real work.

Xray - Amery, WI

They're both idiots.

Bitter Bubble

Before High Definition TV and after.

Boom With A View - Covering my eyes

Jessica, never having touched a mop or a broom in her life, thought she was holding a Golf Club.

Xray - Amery, WI

Is that an attachment in your pocket or are you just happy to see me?

Convertible Boom - Emptying a bag

Who would YOU want to clean YOUR house? (that's a rhetorical question of course!)

Xray - Amery, WI

The resemblance between him and Laura Bush is uncanny!

Bored Boom - Posting a caption that's equally unclever

Oddly enough, Bradley is also Good Housekeeping Magazine's 'Cross Vacuumer of the Year'.

David Winger - Woodland Hills, CA

Tryouts for this year's Victoria's Secret Fashion Show were disappointing.

Boomerick's of Hollywood - In the buff

The resemblance between him and Hillery is uncanny!

Xray - Amery, WI

A revealing look at Bubbles "The Minx" LeRoy with make-up & without.

The Boomarazzi - Filming

It's amazing what airbrushing can do.

All natural Boom - Posing

Wait'll we get our Hanes on you.

Boomerwear - Being briefed

The Wingman auditions for TV Guide's "Look-A-Like" show.

Boom-A-Like - The Twin Cities

This is what happens when you SNIFF too much SWIFFER liquid!

Xray - David... I like your Potato Head caption! LOL!

This guy must be Stoned from Rolling!

Xray - Amery, WI

Father Time was not kind to Jessica.

Tick Tock Boom - Congrats to Larry

Put on a wig and maybe I'd believe it!

David Winger - Woodland Hills, CA

Meet Simpson and Simpson Wannabe. D'oh!

Boom Groening - Springfield

Another member of the hypocritical GOP comes out of the closet and admits he sucks.

BaBoom - Will he become a cheerleader like George Dumbya Bush did?

X-Ray you're right, my mistake...that's Ashley

David Winger - Woodland Hills, CA

Posing for the April issue of Gayblade Magazine.

Xray - Amery, WI

They call him Mrs. Potato Head because he is a woman imi-'tater'!.

David Winger - Woodland Hills, CA

Local man comes "Out of the closet" in style!

Xray - Amery, WI

Barrak Obama's shameless brother showing off to the Press.

Xray - Amery, WI

Jessica Simpson is a HOUSE WIFE????(!)

Xray - Amery, WI

Really desperate housewife!!

David Winger - Woodland Hills, CA

WOW! He's GOOD! I can hardly tell the difference!

Xray - Amery, WI

Can you spot the two Hoover imitators in this picture? Well, the vacuum is really an Oreck. And the man is really named Charles not Herbert.

David Winger - Woodland Hills, CA

"Nick! I'm yours!"

David Winger - Woodland Hills, CA (Love larry's 'brand' of humor, congtats)

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