The 50 funniest Web series

With millions of views and counting, Dan Bialek’s zero-budget videos of knockoff G.I. Joes venting about their armed-forces duties, perceived slights and personal shortcomings is all about the in-joke catchphrases. (Jungle Recon’s “It’s like a mustache with titties!” is a clear favorite.) U.S. military personnel embrace the series as their own, loyally snapping up merch, dressing as favorite characters for Halloween and flocking to the vocal talents’ live shows. Rumor has it a movie isn’t far behind.—JS

Brent Sullivan and Eliot Glazer’s reaction to It Gets Better, the online phenomenon that gives hope and encouragement to LGBT youth, paints a picture of adult gay life that’s not all Madonna and sunshine. They hire drag queens (from divadykes.biz, naturally), visit the free clinic for HIV tests and react to their officemates’ insistence that being gay equals a love for Lady Gaga. As they knock the glitter off gay clichés the public has fallen in love with, Sullivan and Glazer exhibit a winning chemistry while managing not to overdo anything.—ML

Between regular Conan sketches and his The Bitter Buddha documentary, the righteously angry Eddie Pepitone is becoming better known. For several years now, his Monday-through-Friday “live-action, one-panel comic strip” has ceaselessly (relentlessly?) offered concentrated, single-serving bites of the L.A. comic. Every episode involves one anonymous guy trying to enjoy a pudding cup while enduring Pepitone’s rants. Standard break-room humor this is not: This is Pepitone at his ranting, raving, complaining, profaning, uncouth and unhinged best.—JS

Ever get the feeling an instructor’s mind might be elsewhere? At first merely condescending and sarcastic, the unseen Donnie Hoyle’s clenched-jaw hypotheticals eventually allude to his divorce, firing, eviction, grand larceny and flight from authorities. The sight and running gags are dizzying throughout, and the Photoshop demonstrations strangely skilled. After a My Damn Channel full-throttle marketing campaign and a short-lived You Rock at Photoshop “spin-off,” things really began to get weird.…—JS

Appealing to the grade-school boy in all of us, this series speculates endlessly about who would win in a fight between Hitler and Darth Vader, or Albert Einstein and Stephen Hawking. But then it follows through: Each episode pits two titans of history or culture against each other in a verbal jousting match over surprisingly well-constructed beats. Beyond the rapid-fire jokes, the series works because many of the performers, including Zach Sherwin—or MC Mr. Napkins—can actually rap.—ML

Animator Brad Neely does several things well: He creates imposing characters at odds with the status quo; writes simple, catchy songs; and draws cute and expressive illustrations. Put these talents together and you get a series like Super Deluxe’s The Professor Brothers. They’re a pair of profane, self-aggrandizing dudes with ’70s collars and hippie hair who fail as teachers, lovers and prison entertainment. As with all of Neely’s stuff, funny bits of dialogue stand alongside subtle jokes created by well-timed, imaginative edits.—ML

As a money-minded ladder-climber who puts little stock in dreams, feelings or leisurely “conversations,” Lisa Kudrow’s Fiona Wallice conducts truncated headshrinks via webcam. Number of episodes: approximately a billion. Notable guest stars: all of them. Why it won those Webby Awards for Best Writing: no clue, as it’s mostly improvised. Giving hope to underfunded YouTubers everywhere (and keeping Kudrow relevant post-Friends), Therapy was picked up for bona fide TV airings in 2010.—JS

This tentpole CollegeHumor series stars two of its employees with a natural rapport and shared whimsical sense of humor. Each episode has a theme, but over the years, it’s the core relationship between the title characters that has really stood out, inviting viewers to see themselves in these two weirdos and potentially think of them as friends. Jake and Amir predates the podcast explosion (which purports to do the same thing for comedians) and remains a consistent part of CollegeHumor’s free-for-all repertoire.—SH

What happens behind the closed doors of the teachers' lounge? Comedians and series creators Ted Alexandro and Hollis James give you an inside look as they portray a music teacher (Alexandro) and a janitor (James) while hanging out in their star-studded faculty lounge. Expect to meet the gym teacher (Judy Gold), head of security (Jim Norton), head of the talented-and-gifted program (SNL’s Michael Che), school photographer (Dave Attell), the nutritionist (Jim Gaffigan), the principal (Lewis Black), and get to hear announcements by Janeane Garofalo and Alec Baldwin. Each episode leads you down a hilarious, unexpected road filled with killer bits all written by stand-up veterans.”—TB

Colin Quinn plays a washed up caricature of himself in this fake behind-the-scenes look at a network cop drama written by and staring Quinn’s alter ego, a terrible writer/actor that uses the show as a platform to hop on various bandwagons, like having Amy Schumer play a hipster twentysomething, because Girls is popular, right? He also uses the show as an excuse to air grievances (publicly telling Michael Che that he only has Quinn’s old desk job (SNL’s “Weekend Update”) because Quinn wanted to leave is a particular highlight). With about six minutes an episode, it’s long enough to satisfy your joke cravings, but short enough to make you want to watch more.—TB

Married duo Ben Sinclair and Katja Blichfeld (Emmy Award–winning casting director for 30 Rock), created this beautifully shot Web series with comedic inspiration from Party Down and Six Feet Under. Each episode follows an NYC pot dealer named the Guy (Sinclair) as he delivers weed to a new client. The characters he deals with in each episode perfectly poke fun at the many flavors of modern New Yorkers while also embracing their unique quirks. The show will shortly be making a jump from web to TV since HBO loved it enough to order a six-episode season. —TB

A highly deserving respite from this painfully Caucasian list, Misadventures is a slow, cerebral and well-observed trip into the mind of the titular awkward black girl, J. It delves into J’s work life, love life (often revolving around fellow socially unrefined soul White Jay), and her deep and abiding love of writing raps. The smarts and ease behind the show, provided by its creator and affable star, Issa Rae, ensured that it raised enough money through Kickstarter to produce its first season before moving to Pharrell Williams’s YouTube channel, i am OTHER, for season two.—ML

Set in an Ikea during working hours, this part overblown soap opera, part heist film involves sneaking in scenes when staff members aren’t watching and interacting with those who do. The people working to put Ikea Heights in motion need to prepare not only tightly scripted scenes, but multiple backup plans in case things go poorly—and no episode misses its mark. Even sending hordes of people in zombie makeup into an open Ikea has yielded funny results. Ikea Heights may not be super tight from a production-quality perspective, but it’s admirable for its ambition and frantic, silly execution.—SH

“In the year 2117, an eight-year-old gay boy named Shannon found a magic lamp.” So begins Planet Unicorn, a sugary-sweet animated series that results from Shannon’s third wish: a planet full of unicorns. It’s equal parts head-scratching and tickling, made all the more compelling by its commitment to the initial over-the-top premise. There is nothing quite like watching gay unicorns, one of which is named Tom Cruise, have adventures in a blindingly pastel world to make you realize that Web series are receptacles for ideas big and small, odd and very odd. Heeey, if it ain’t broke…—SH

In their chatty episodic series, comedy duo Ilana Glazer and Abbi Jacobson present a character-filled New York City shared by two self-absorbed girlfriends. Whether they’re judging hipsters at McCarren Park or dating guys for their washer-dryers, the fictional Abbi and Ilana make cheerful and companionable guides whose imperfections have endeared them to more viewers than just us; Since being picked up by Comedy Central, the duo have skyrocketed to the top of the comedy world.—ML

Anyone whose reference point for TV lesbians is The L Word would do well to delve into the world of the self-described “superficial, homophobic” couple of The Slope. Over two seasons, Ingrid and Desiree slowly break up as they slurp Gorilla Coffee and argue the finer points of tops versus bottoms and the relative hotness of white babies. The show is anchored by solid writing and great performances from Desiree Akhavan (as the chattering, daffy Desiree) and Ingrid Jungermann (as the dry, incisive Ingrid). Since The Slope ended in summer 2012, it has spawned Jungermann’s worthy offshoot, F to Seventh, and Akhavan made her directorial debut with the excellent indie movie Appropriate Behavior (in which she also stars).—ML

This understated, ongoing series follows up-and-coming comedians as they do the mundane things comedians do: The world’s calmest and strangest human, Rory Scovel, goes on the road; the giddily absurd Kurt Braunohler writes silly messages on greeting cards and puts them back on the shelf. Lots of attention gets paid to bigger-name comics in the national press, but this multipart documentary, created by Scott Moran, shows what it’s like to exist in the trenches—in clubs and the backrooms of bars—and captures the inherent liberation and terror of not knowing what’s next.—SH

This My Damn Channel production from current The Tonight Show Starring Jimmy Fallon head writer A.D. Miles took the episodic soap-opera genre, boiled it down and exploited all of its clichés—high-stakes plot points like murder and marriage, overly dramatic music, tight close-ups, bloated acting—in the course of 10 episodes. The giddy result, which stars Miles himself alongside other recognizable names like Joe Lo Truglio, starts with a woman being strangled by her sweater and ends with a turd in the punch bowl, literally.—ML

For those who think Dr. Horrible isn’t out-there enough, this Neil Patrick Harris and Jim Henson Company collaboration features its near-narcoleptic lead explaining that he dreams “in puppet,” immediately falling asleep, and then punning it up in green-screen dreamscapes among abducting-alien puppets, TV-crime puppets, Bollywood puppets and doctor’s-office puppets shocked by the strange medical anomaly between Neil’s legs. It’s fast-paced, imaginative, devilishly un-family-friendly and, like all the best flights of unconscious fantasy, over far too soon.—JS

Syd Field–worshipping screenwriters Clark Duke and “Mikey Cera” (played by Clark Duke and Michael Cera, naturally) will sell a TV script. This is a fact. So naturally, they hire a crew to film their long, painfully awkward journey for posterity. Somewhere between the Clark and Michael pilot—Duke’s school thesis—and the nine subsequent, CBS-sponsored episodes, Patton Oswalt, Jonah Hill, David Cross, Andy Richter, Tim and Eric, and Arrested Development creator Mitch Hurwitz showed up to help this summer 2007 mockumentary raise discomfort levels to new, er, lows.—JS

Another early Funny or Die hit, Drunk History gets a comic—such as Jen Kirkman or Duncan Trussell—ripped and has him or her recount a significant story in American history. Actors re-create the events described, even aping the comedian’s sloppily invented dialogue (Aaron Burr to Alexander Hamilton: “Hey, you’re givin’ me shit, we gotta duel”). The fun here is watching the juxtaposition between the soused storyteller’s self-conscious attempt to keep from blacking out while reenactors play their parts as straight as an arrow.—ML

Pete Holmes is best known from his popular podcast You Made It Weird with Pete Holmes, but he first launched into the digital sphere with Front Page Films, a collective he formed with comic Matt McCarthy and writer-director Oren Brimer. Though we love their take on the Christopher Nolan Batman films, Badman, the trio’s Kid Farm is our favorite. Amping up the traditional family values with which Holmes was raised, the series finds its stellar cast—playing kids and those in their orbit—to embracing the ridiculousness of living in a home where they can’t help but literally trip over their brothers and sisters. It’s textbook comedy of extremes, with a creepy-pastor next-door neighbor thrown in for good measure.—SH

The closest thing to a full-on televised serial that the Web has been able to dream up thus far, The Guild’s six seasons follow the interpersonal entanglements of an online gamers’ group and boast quirky yet complex characters, engaging plotlines and ex–Star Trekker Wil Wheaton as a bad guy. Who’da thunk a series about geeks with depth, heart and mad skill points would do so well on the Internet? (Well, creator-writer-star Felicia Day, for one.)—JS

The only selling point missing from the self-explanatory title of Crackle’s humor-and-hubcaps history lesson is the name of its host, Jerry Seinfeld. The comedian proved the experiment has less to do with the classic Volkswagens and Benzes he carts his comic pals around in, and is more about extending his legacy beyond the realm of network-sitcom-dom. As long as he continues to glean leisurely, aw-shucks industry wisdom about longevity, sacrifice and discipline from high-wattage talent like Larry David, Carl Reiner and Ricky Gervais, there’s no reason to think he won’t.—JS

David Wain’s pet project, a My Damn Channel production, is a thinly veiled excuse for him to make out with all sorts of beautiful women—Lake Bell, Elizabeth Banks and even his wife, Zandy Hartig. It’s also an infectious and charming commentary on modern dating, with Wain always willing to play the fool. He takes things to extremes, uncomfortably throwing himself into the middle of a fight with a gang, only to be surprised when he punches through one of the thugs. He may have moved on to directing big-budget studio pictures, but Wainy Days remains a time capsule of his young, wide-eyed self, making his friends laugh with unexpected jump cuts and heightened, ’80s-movie-style silliness.—JS

Each episode of Periods takes characters from a touchstone work of literature (Ethan Frome, say), or a historical clique (Pilgrims, for instance) and fills their mouths with elliptical, modern speech. More than tossing in some likes and ums, though, the Periods crew’s attention to detail is unsurpassed: The costumes, sets and performances are all stellar, and each episode has its own genre spoof tucked away in it—the girls of Little Women get catty via vlogs; Adam and Eve are on a reality show with God (“Hiii, I’m Eve, I’m 24, and I’m from Adam’s rib”).—ML

Before certain SNL digital shorts made Sunday lazy and put their dick in a box, the burgeoning collective known as Lonely Island—Andy Samberg, Jorma Taccone and Akiva Schaffer—created a schizo, throw-it-against-the-wall-and-see-what-sticks teen melodrama with twists (addiction! kidnapping! suicide!) as clichéd as the budget was nonexistent (a tan sheet = the beach! silver-sprayed cardboard = ninja stars! a puppet = absent lead Sarah Chalke!). Though things imploded after seven episodes, happily, due to lack of time: Lorne Michaels had come a-calling.—JS

The odd comedy brain of SNL writer Michael Patrick O’Brien ensures that his celebrity talk show, which takes place in a closet, sidesteps the standard Q&A in favor of something much more surprising and entertaining. The tight environs, presence of booze and weird topics (“Please talk about all the ways you are or are not similar to a horse”) make the proceedings light, improvisational and silly—even when O’Brien hosts Insane Clown Posse, of all people. Of course, there’s a potential make-out session with every guest, from Amy Poehler to Jon Hamm.—ML

From 2005 to 2008, Comedy Central parodied Viacom sibling VH1’s many talking-head series (I Love the ’80s et al.), employing black-and-white footage, such episode themes as “Prohibition,” “The Lindbergh Baby” and “The Great Depression,” and introducing hot up-and-coming talent like John Mulaney, Chelsea Peretti, Nick Kroll, Andrés du Bouchet and Julie Klausner as jazz musicians, society columnists, crooners, drifters and…Alfalfa. A telling moment from the “1936 Berlin Olympics” episode involves Adolf Hitler telling Jesse Owens, “You can run a race, but I can destroy one!” Hey-o!—JS

Surrealist alternative comic Maria Bamford picked one of her many fears—moving back in with her parents in Duluth, Minnesota—and faced it by acting out how the scenario might unfold. Or acted out who, perhaps; over two seasons on the Super Deluxe, Bamford concocted an engrossing story arc using only impressions of said parents, her sister, high-school friends and even a gentleman caller. Convincing and quirky, this series, which left viewers wondering if they were legitimately witnessing the Bammer’s mental breakdown, is required viewing for the self-doubting and the displaced.—JS

Writers and stars Nick Ciavarella, Jared Warner and Tim Dean—all founding members of sketch group Murderfist—bring a deliriously enjoyable weirdness to this show based on the simple premise of “dude tries to find a date.” Skewering the twentysomething New York lifestyle for men in much the same way Broad City does for women, episodes veer from hysterical drunk party antics to kidnapping, literal blind dates and an awesome takedown of the New York improv scene. The natural onscreen chemistry between the guys gives even the darkest moments an odd charm, but most important of all, it’s completely hilarious.—NL

A mockumentary version of E! True Hollywood Story, Yacht Rock charted the mythological songsploits of Michael McDonald, Kenny Loggins, Steely Dan & Co. in 10 Channel 101 episodes over five years. Not only did the exaggerated effects and over-the-top dramatics of the mellow-oldies soap opera usher the titular genre into the pop-culture lexicon, but a bewigged Jason Lee, Drew Carey, Dan Harmon, Wyatt Cenac, Steve Agee, James Adomian and Matt Braunger appeared throughout to, as always, keep it smoooth.—JS

If anyone has tapped the true power of Auto-Tune, it’s the Gregory Brothers. This quartet began by finding news items both noteworthy and ridiculous, and using the musical tool to robotically harmonize the voices of newscasters and politicians into amazingly catchy songs they created. In 2010, the local-news–oriented “Bed Intruder Song” became the flash point that led to spin-off series Songify This, which creates melodies based on viral videos by stars such as Charlie Sheen and random uploaders like the guy who saw a double rainbow all the way across the sky. They even make politics fun: They found success in condensing and framing the 2012 presidential debates in song.—ML

In the mid-aughts, Billy Eichner was doing his On the Street videos—in which he accosted New Yorkers to ask them about politics and pop culture—to fill a segment at his live Creation Nation show. After moving to Funny or Die (and then to Fuse), his gonzo tactics only ramped up as he mowed down old ladies for not knowing who was nominated in the Oscars and cursed just about anyone for not liking Meryl Streep enough. The combo of Eichner’s frenetic, undaunted blasphemy and New Yorkers just being themselves makes every video, at some point, cackle-inducing.—ML

While its sister series, Childrens Hospital, made the jump to television, Burning Love is perfectly situated as a semiweekly Yahoo Web series. It’s a grand spoof of The Bachelor and The Bachelorette, after all: a show known to pad its running time with plenty of unnecessary background information about its contestants (like the woman from last season’s Bachelor who unironically wore vampire teeth) and shots of its protagonist wistfully staring out a beachside window. Burning Love turns its contestants—comedy royalty like Ken Jeong, Colin Hanks and Kristen Bell—into heightened caricatures such as Jeong’s Ballerina, a very poorly hidden transgender contestant. And the stars of the series, first Ken Marino and then June Diane Raphael, masterfully play the lothario while simultaneously commenting on the whole phenomenon.—SH

Before there were Web series, there were short films. Stella, the ex–State trio of Michael Ian Black, Michael Showalter and David Wain, made more than two dozen, which were projected during their 1997–2004 live shows. The shorts later found another, larger audience online, and are now housed in CollegeHumor’s library. Before Stella landed a show on Comedy Central, these shorts highlighted Black, Showalter and Wain’s talent for playing exaggerated, infantile versions of themselves. Forever dressed in suits, they hung out with pre-fame Paul Rudd, Bradley Cooper, Elizabeth Banks, Sam Rockwell and Julie Bowen, and mock-humped everything in sight. They also threw in random dildos… lots and lots of random dildos.—JS

Elaine Carroll’s fleet, goofy series proves that the narrowest focus often yields the most results. Carroll plays Mary-Kate Olsen, who, over the course of a handful of seasons, refuses to see that her spoiled, silver-spoon upbringing isn’t doing her any favors. The minutiae of her obnoxious behavior gets put under the microscope, giving Carroll plenty of opportunities to show off her attention to detail, heightening real-life personality quirks and mixing them with those of her own invention. (Even the character’s voice is an odd, slurred combination of reality and fantasy.) Very Mary-Kate is distinctly compelling because it doesn’t try to leave the world of Mary-Kate Olsen—only find new and exciting toys to play with—and is tightly written, running about two minutes an episode.—SH

Before the term Web series was synonymous with YouTube, the team behind Homestar Runner was making animated shorts in Flash that starred a bevvy of odd characters—the strangest being a grizzly-voiced luchador easily half the size of everyone else. This was Strong Bad, and his bitterness plus his propensity for verbal sparring made his email-response videos—acting out the answers to real questions—a prime example of spinning the mundane into something surreal. Typos turned into inspiration triggers, challenges were always accepted, and the series became the clearest distillation of the Homestar try-anything spirit. Strong Bad also became a kind of mascot for episodic Web content, proof positive that if you put the time and effort into your craft, people will check back every week.—SH

What was the best thing to come out of the 2007–08 writers’ strike? A Hulu-housed, Neil Patrick Harris–starring, Joss Whedon–directed and -cowritten trilogy that proved Web series could be flat-out epic. The tale of a wayward scientist hoping to impress Evil League of Evil head Bad Horse (the Thoroughbred of Sin…portrayed by an actual horse!) was part traditional musical, part supervillain origin story and part impossibly clever, surprisingly heart-wrenching tragicomedy, and went on to spawn a digital soundtrack, comic books and amateur stage shows. A sequel was shot in the spring of 2013 and aired on the CW network later that year.—JS

The simplest ideas are always the best ones, and so goes Zach Galifianakis’s fascinating case study of awkwardness and the Web series with the broadest, most lasting impact. Guests like Steve Carell are brought in and sat down on a stark black stage between two ferns, and Galifianakis grills them to their breaking point. Not only did Ferns help make Funny or Die’s name, it rapidly shaped the way Web series were viewed and created without losing its lovable shagginess. Whether he’s interviewing the President of the United States of America, Oscar winners or low-level celebrity friends, either as an underappreciated comic or the linchpin of the Hangover film franchise, Galifianakis channels the uncomfortableness like a freakin’ lightning rod, and Between Two Ferns’ integrity remains intact. Its ramshackle nature is also the definitive call to arms for anyone on the Internet with a great idea: Do it! It’s a lot easier and more rewarding than you think.—SH