A Look Back at the Funniest Moments on Mad Men


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It’s the end of an era — bygone or not. This Sunday marks the final episode of the critically acclaimed, award-gobbling powerhouse Mad Men. Just shy of 100 episodes, the series captured all the major social, political, business, and sexual issues of the ’60s and ’70s and deftly related them to the topics of today. Without a doubt, Don, Peggy, Roger, Joan, and the rest will be sorely missed and will leave behind a heart-shaped hole in our programming schedules.

But as the seventh season draws to a close, and with it the lives of a few dozen characters as familiar as close family members, we take a look back at the 10 funniest and goofiest moments immortalized in animated GIF form.

10. Peggy’s Personal Roller Derby

10. Peggy Skating
Backed by a boozy Roger on the organ, an equally tipsy Peggy glides across the frame on a pair of roller skates as carefree as a pixie. Encapsulating the dizzy, grinning state right before passing out, it’s the perfect GIF to express a fun and innocent night of binge drinking.

9. Roger Finds a Soulmate

9. Roger Drinking Bird
And speaking of drinking, Mad Men did little of anything but. Set in a time when folks washed down their corn flakes with gin, the show was essentially a substance abuse group meeting with a wardrobe budget. And here, Roger finally finds a drinking buddy that could actually keep up.

8. Ken Busts a Move

8. Ken Dancing
Feeling the high of a speed-based cocktail, this tap dancing Ken Cosgrove GIF is a delight. Appropriate for caffeine-fueled all-nighters or the tackling a bevy of errands with the energy of a freight train, this image celebrates the elation one feels after finishing all your work for the day.

7. Pete Gets Decked

7. Pete Punched
Second only to Tyrion slapping Joffrey, this GIF of Pete Campbell getting punched nails that cathartic Schadenfreude of seeing a disliked character getting hurt. And after insulting Lane Pryce, cheating on his wife, and being just a general douche, we’d gladly let this image loop more than a few times.

6. Roger Shimmies Down the Hall

6. Roger Dancing
With no shortage of stunningly beautiful women on the show, who would’ve thought the most lithely sensual dance would be delivered by John Slattery? Seductively singing “Frère Jacques” with the passion of a French escort, Roger can clearly hold his own against an office filled with conga-dancing dames.

5. Don’s Mock Crying

Don wah wah gif

Got a friend who’s complaining about their $80,000 job or having to clean their 3,200-square-foot apartment? Well, here’s a GIF that could add a little introspection to their Facebook wall. Succinct and to the point, its only downside would be the image’s prevalence in online political arguments.

4. Don’s Actual Crying

Don crying mad men

But as snark gives way to sincerity, occasionally we need a picture that depicts our protective walls crumbling as we surrender to despair. That, and it’s pretty funny to see Jon Hamm weeping. Even for someone who oozes cool masculinity out of every pore, sometimes a guy just has to turn on the water works.

3. Pete Takes a Tumble

3. Pete Falling
We all know what it’s like to have tempers flare beyond our equilibrium, and this GIF of a furious Pete stumbling down the stairs is a fantastic representation of being “too angry to stand.”

2. Roger’s Liquid Lunch

2. Roger Vomiting
Who hasn’t overindulged a bit during a work lunch? We can all relate to being a little too tipsy on the way back to the office, right? And how many times have we regurgitated our entire meal and drink orders in front of important clients? Too many to count! So for all of us who’ve blown multimillion-dollar deals because of one bourbon too many, this GIF’s for you!

1. The Lawnmower Reaction

1. Lawnmower
Arguably the most memorable moment in Mad Men’s entire run also makes for one fantastic animated GIF. Something as small and incidental as a runaway riding lawnmower driven inside an office can completely change the way a man walks for the rest of his life. It also ain’t too pretty for the bystanders drenched with an arterial spray. Still, as horrific surprises go, this one’s pretty damn funny.

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Documentary Now! Robert Evans Mansion

The Reel Deal

Everything You Need To Know About “Mr. Runner Up” Inspiration Robert Evans

Watch the two-part finale of Documentary Now! this Wednesday at 10P on IFC.

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Photo Credit: Everett Collection

In its upcoming two-part finale, Documentary Now! spoofs the crown jewel of docs: The Kid Stays In The Picture. It’s the autobiographical documentary about Robert Evans, the unlikely Hollywood mogul whose mix of self-aggrandizing bravado, classic good looks and extremely circumstantial good luck took him from being a salesman to an actor to the head of Paramount Pictures.

If you’ve never seen the film, it’s totally worth it. Rotten Tomatoes agrees, with a staggeringly-high approval rating. Watch it before, or watch it after — doesn’t matter. You’ll appreciate it whenever.

In the meantime, here’s a bit of background that will come in handy…

Robert Loves Robert

Robert Evans desk

USA Films/Everett Collection

Robert Evans is the ultimate Robert Evans fan. The movie was narrated by Robert Evans and based on his memoir of the same name. It is totally unbiased.

He’s Kind Of A Big Deal

Robert Evans, Chinatown
Paramount Pictures

Evans produced some of Hollywood’s true classics: Chinatown, Rosemary’s Baby, The Godfather, Love Story…the list goes on. Totally legit and amazing movies.

He’s Also Kind Of A Joke

Wag The Dog
New Line Cinema

Evans has been parodied in TV shows and movies like Entourage and Wag The Dog. He is the quintessential “producer” you already have in your head.

So Wrong He’s Right

Robert Evans Slap
20th Century Film Corp

Robert Evans is a notorious narcissist whose love of self is so blind and sincere that it’s actually adorable.

There’s Something Missing

via Giphy

Entire sections of Robert Evans’ life are left out of the documentary. Maybe it’s because of timing. Maybe it’s because real life isn’t a tidy narrative. Who knows.

He Blew It

Spider coke

Evans had a pretty spectacular fall from grace. He was convicted of cocaine trafficking in the early 80’s, and was connected to a contract killing during the production of The Cotton Club. Oops.

Losing Is For Losers

Everett Collection
Everett Collection

In the Robert Evans mythology, all tragedies are just triumphs in disguise, and every story has a happy ending…for Robert Evans.

Bill Hader Jerry Wallach

With these simple facts in hand you are now prepared to thoroughly enjoy the two-part finale of Documentary Now! starting this Wednesday at 10/9c on IFC.

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Weird Roles

Anthony Michael Hall’s Most Rotten Movies

Catch Anthony Michael Hall in Weird Science on Friday at 8P on IFC.

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Photo Credit: Universal/Everett Collection

Anthony Michael Hall was the quintessential ’80s nerd. We love him in classics like The Breakfast Club and National Lampoon’s Vacation. But even the brainiest among us has his weak spots. In honor of Weird Science airing this Rotten Friday, we analyze Hall’s worst movies.

Weird Science (1985) 56%

A low point for John Hughes, Weird Science is way too wacky for its own good. Anthony Michael Hall’s Gary and his pal Wyatt (Ilan Mitchell-Smith) create the “perfect woman.” Supernatural chaos ensues. The film costars a young Bill Paxton, floppy disks, and a general disconnect from all reality.

The Caveman’s Valentine (2001) 46%

This ambitious drama starring Samuel L. Jackson couldn’t live up to its rich premise. Jackson plays Romulus, a Juilliard-educated, paranoid schizophrenic who lives in a cave. Hall co-stars as Bob, a rich man, who wants to see Romulus play the piano. The plot centers around Romulus investigating a murder, but with so much going on, the movie never quite finds its rhythm.

All About the Benjamins (2002) 30%

Ice Cube plays a bounty hunter who teams up with Mike Epps’ con man to catch diamond thieves. Hall plays Lil J, a small-time drug dealer. It’s definitely a role we’ve never seen Hall in, but overall the movie isn’t funny or original enough to justify its violence.

Freddy Got Fingered (2001) 11%

This showcase for Tom Green’s goofy gross-out comedy is often hailed as one of the worst films of all time. Green plays Gord, a 20-something slacker, who dreams of having his own animated series. Hall is Dave Davidson, a CEO of an animation studio who eventually helps Gord find success. Too bad Tom Green wasn’t so lucky.

Johnny Be Good (1988) 0%

Hall plays against type as Johnny Walker, a star quarterback. Robert Downey Jr. is his best friend and Uma Thurman plays his devoted girlfriend. Despite the support of a future A-list cast, the movie lacks central conflict and charm. Or, as TV Guide put it, “Johnny be worthless.” Ouch.

Catch the “Too Rotten to Miss” Weird Science this Friday at 8P on IFC.

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Season 6: Episode 1: Pickathon

Binge Fest

Portlandia Season 6 Now Available On DVD

The perfect addition to your locally-sourced, artisanal DVD collection.

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End of summer got you feeling like:

Portlandia Toni Screaming GIF

Ease into fall with Portlandia‘s sixth season. Relive the latest exploits of Fred Armisen and Carrie Brownstein’s cast of characters, including Doug and Claire’s poignant breakup, Lance’s foray into intellectual society, and the terrifying rampage of a tsukemen Noodle Monster! Plus, guest stars The Flaming Lips, Glenn Danzig, Louis C.K., Kevin Corrigan, Zoë Kravitz, and more stop by to experience what Portlandia is all about.

Pick up a copy of the DVD today, or watch full episodes and series extras now on IFC.com and the IFC app.

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