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Web series and online sketches

Why trek all the way to a comedy club when you can see the city’s funniest online?


It’s winter, dammit, and no matter how much we love it when improv troupe Katydids delivers 20 minutes of high-stakes nuttiness or when the brainy weirdos at Kill All Comedy hit us over the head with unexpected, WTF sketches, many of us are hiding happily under our covers. But thanks to an ongoing trend in comedians creating Web-based content, you now have the choice to see the city’s funniest with a mug o’ (spiked) cocoa from the comfort of your own comforter.

Ted Tremper, a local comedian whose painfully funny and award-winning improvised Web series Break-ups I loved, returned in 2012 with Shrink. Also improvised, Shrink stars Tim Baltz (Second City, iO) as a wannabe therapist who sees patients out of his garage and delivers incredulous looks and awful responses when his patients offer up their most intimate secrets (Baltz is perfectly cast). Both the pilot and subsequent webisodes are peppered with a brilliant cast of top-notch Chicago comedians past and present including Annoyance founder Mick Napier, Emily Wilson (Cougar Town), Aidy Bryant (SNL) and more.

I was jonesing for more of sketch and improv troupe Warm Milk after it charmed me with its all-Gaga mariachi cover band at Sketchfest. That request is partially filled by “Fiscal” Cliff Thompson (, keywords: Dan Bulla), a new collection of shorts in which ensemble member Bulla dons crooked spectacles and a gaudy sports coat and dispenses dubious financial advice. Searching under Bulla will also take you to a series called He’s A Great Book! With Ozzie Guillen cocreated with Warm Milk’s Jasbir Singh, in which Singh hilariously portrays the outspoken former baseball coach as he dishes on literary classics.

I love watching Katie O’Brien make googly eyes at a hot dad or witnessing a smackdown between Katie Thomas and SNL’s Cecily Strong on Teachers, a 14-episode Web series that debuted in November and just signed a new deal with The Onion for additional episodes. Teachers shows the underbelly of public schools, finding comedy in faculty cliques, obsessive parents and vacuous educators. It features the entire cast of the Katydids (Wednesdays at the Annoyance), which also include Caitlin Barlow, Katy Colloton, Cate Freedman and Kate Lambert.

The Kill All Comedy crew kills it hard twice monthly at both the Upstairs Gallery and Quencher’s Saloon and has tiptoed into Web content with hilarious sketches like “Dadz,” a parody of straight men’s obsession with fixing things, and the brilliant “Movie Boyz,” in which Gary Richardson tries to sneak into an R-rated movie. Watch them both now.

Entertainment entrepreneur Jake Sasseville pokes fun at his own fame seeking in the Chicago-set, full-length webseries Delusions of Grandeur. Episodes are TV length and could stand to be trimmed, but they’re packed full of funny Chicagoans like Tara DeFrancisco (iO’s Deltones) as a network exec and Sasseville’s foil, plus Carly Olson (iO’s Wonderbat, ComedySportz) and Nnamdi Ngwe (iO’s Chaos Theory and Barack All Night) in supporting roles.

In the new monthly Web series Making New Friends (, keywords: peaches and hot sauce), Patrick O’Rourke (Making New Friends podcast) and Zack Mast (iO’s Wussball) play two slacker dudes (no surprise there) who get into all sorts of trouble from the comfort of their apartment. Happily, each episode is short, slickly produced and wonderfully absurd in its constant heightening and raising of stakes.

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