Rachel Dratch, Chris Gethard, Amy Schumer

Taking apart any sketch reveals the same bare bones structure: a situation and/or character gets more and more absurd until there’s no bigger place to go. The sharpest sketches, though, will pull out a last minute turn that makes you reevaluate the entire thing. Pulling the comedic rug out from under the initial concept is what made a sketch like “Football Town Nights” so successful; it wasn’t just about football players not understanding that they probably shouldn’t rape people, but about how the aggressive way Josh Charles’ coach talks to them about taking what’s theirs on the field eerily echoes the sexual assault he was originally warning against. “Wingwoman” doesn’t have any sketches quite on “Football Town Nights” level, but it has its moments, many of which come thanks to that last minute “wait, what?” moment.

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This definitely holds true for “Listen Alert,” the opening infomercial sketch that promises to provide an on-call listener whenever your partner checks out (“for just $100,000 a month!”). At first it seems like another sketch about how men zone out while women talk, but then Schumer’s reassuring voiceover lets us know that “this isn’t just for women.” Cut to: a dude at dinner going on about the moment when his height caught up to his shoe size while his date scrolls through her phone and a Listen Alert employee listens with baited breath for the thrilling conclusion. Then, the first woman we saw dial Listen Alert (the show’s head writer Jessi Klein) tries to tell a representative about her dream, and the voiceover cuts her off with an irritated snap. “We will not listen to your dreams! We’re not saints.” So in the end, the sketch isn’t about chatty ladies and bored dudes, but how everyone has boring shit they want to talk about, but the only way anyone should have to hear it is if they’re getting paid $100,000 a month.

Same goes for the anal sex sketch (this is a fun show to review), which starts off as typical as possible before ending on an unsettling and completely bizarre note. Amy brings her new boyfriend (Trainwreck co-star Mike Birbiglia) to meet her brother, who immediately starts in on the “you better not hurt my sister” routine. Mike’s ready for this, but he’s definitely not ready for the next step, which is Amy’s brother pleading with him to promise that he’ll never have anal sex with his sister, even when she inevitably begs for it (“we’re from Long Island!”). This escalates and escalates until finally, Mike meets his girlfriend—who was paralyzed when Amy’s brother had anal sex with her, which…wait, what?

Two promising sketches fall a little flat because they don’t ever get beyond the final “get bigger!” step. The titular “Wingwoman” has a newly married Amy getting way too excited about her friend’s newly single status. “I’ll be your wingwoman!” she squeals, as Caroline (Rachel Dratch, this reviewer) cringes. Amy’s first stab at wingwomanhood has her grabbing at Chris (Gethard), and while she says she’s doing it for Caroline, her method just ends up being flirting her ass off while the friend she’s supposed to be hooking up gapes in horror. It’s a typically smart observation from the Inside Amy Schumer writers room, which has a knack for pinpointing some of the more unflattering truths of internalized dating bullshit, like married women living vicariously through their single friends. But the only place “Wingwoman” ends up going is into Amy’s pants while Caroline shakes her head and walks away. Funny concept, but it doesn’t quite stick the landing.

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The same goes for “Salem Witch Trials,” a great concept that never quite goes anywhere unexpected or even very interesting. Goody Amy and Goody Bridget (Everett) are on trial for “hexing” the male population of the town with mysterious penis ailments, i.e. sexually transmitted diseases. The men are played by some reliably funny comedians, including presiding judge Colin Quinn (also one of Schumer’s Trainwreck co-stars). It’s hilarious to see how the hysterical men accuse the women of witchcraft while simultaneously complimenting their skills (they’re predominantly lefthanded, but still pretty awesome with both hands! Witch!!). But the sketch still ends on a limp note, as Goody Amy and Goody Bridget whisper inevitably sexy nothings into Quinn’s ear, causing him to kick everyone out with haste so he can conduct a “private burning” with the two witches. It’s not bad, but it’s not especially thrilling, either.

That all being said, though, the most successful sketch of the night never really goes against its own grain, but justifies the straightfoward escalation of absurdity with sharp and unexpected jokes. “Time Travel” features several time traveling Amys talking to 2015 Amy right as her gross boyfriend says they should move in together. It starts with Six Years From Now Amy telling her that her boyfriend is going to give her gonorrhea and bedbugs (Amy: “Ew, I’ve never had bedbugs!”). But then the Amys just keep coming, and they keep saying that for some ridiculous reason, her relationship with this dude is the crux of just about every potential disaster in the known universe. If she doesn’t give this guy a bathroom blowjob, ebola will take down everything. Millions will die! The bit goes as far as it can - one of the last Amys to show up is a futuristic assassin with a laser gun - but still ends with present day Amy vaporizing the boyfriend when his future self says she’s going to get fat, anyway. No wait, scratch that: it ends with present day Amy meeting Five Years From Now Amy, who is totally pulling off bangs. It’s an incredibly silly sketch without much of a real twist off its own formula, but when there are three sharp jokes for every surreal moment, who cares?

Stray observations:

  • Note: Simultaneous thanks to Kate Knibbs for letting me sub in and apologies for the late review are in order. I didn’t know I was volunteering to review something the night a prohibitive blackout swept my part of the city, but it sure kept things wacky! (I tried - and failed - to eat a pie to save its life.)
  • The standup portion was brief but on point as Schumer talks about how she’s seen as “a sex comic” even though dude standups could “whip out their dick” and still be looked at as “a thinker.”
  • The “Amy Goes Deep” segments are always hit or miss, and unfortunately tonight’s interview with a former Amish woman doesn’t end up doing much, even with the explanation of “bed courtship.”
  • Married Amy got married in a destination wedding in the middle of nowhere on New Year’s Eve. Married Amy is the worst.
  • ”Oh my god, I can’t kill someone who’s willing to sleep with me!”

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