Disconcerting fact about Pete Holmes: he voices the baby on those irritating E-Trade commercials. Other than that, though, he’s a pretty engaging comedian who seems comfortable in his neurotic skin. Unlike his glum, lethargic peers, Holmes sweats for his jokes, yukking it up and welcoming his audience into a progressively more interactive set. On his 2011 album, Impregnated With Wonder, he comes across as a 32-year-old white male bitterly shaking his fist at a broken world—then realizing he’s only got 32-year-old-white-male problems and making fun of himself because it’s the right thing to do. Holmes’s animated, sometimes exasperated material touches on having to pretend to like museums and how Facebook has gone out of its way to make privacy uncool. His ability to seem genuinely verklempt with each joke—completely shocked by society’s conventions—hooks us; we help him build his shoddy bridge of logic and cross it with him, laughing and nodding and thinking, “Yes, you’re right, Pete, having Google on smartphones really is ruining lives.” Fri-Sat 10/5-10/6, 8 and 10 PM, Lincoln Lodge, 4008 N. Lincoln, 773-251-1539, thelincolnlodge.com, $15.
I learned long ago never to strap myself into a spinning carnival ride. All it gets you is a dizzy headache and puke everywhere, on everyone. Mike Birbiglia had to learn that lesson the hard way, by heaving up soda and cotton candy while riding the Scrambler during his first boy-girl date, in seventh grade. Vomit plus time equaling comedy, the episode makes for a funny yarn when he tells it as part of his latest comic monologue, My Girlfriend’s Boyfriend.
Birbilgia will perform Boyfriend here in October, when he makes good on his promise to return to Chicago after having canceled his Just for Laughs Festival shows last June. The piece is a sequel to his wildly popular Sleepwalk With Me (which became a book and now a movie) and follows him through a series of coming-of-age—and of-age—blunders involving the opposite sex. Onstage, Birbiglia radiates a self-deprecating sweetness, taking jabs at his own ineptitude on subjects that range from teenage make-out sessions to meeting the titular, actually pretty cool boyfriend (surprise!). It’s cute, honest, and embarrassing—and Birbiglia gets palpable enjoyment from retelling it all. 10/25-10/29: Tue-Thu 7:30 PM, Fri-Sat 7:30 and 10 PM, Victory Gardens Biograph Theater, 2433 N. Lincoln, 773-871-3000, girlfriendsboyfriend.com, $45.
Do three minutes on the Facebook fan page for Red Lobster’s life-affirming cheddar bay biscuits and chances are solid I’m going to buy whatever you’re selling. Former Chicagoan Kyle Kinane is every stoner dude’s dude, working a comedy-club crowd the same way your funny friend used to work the round table of burnouts that huddled in your parents’ dank basement, bong in tow, every day after high school. A little gruff, a little slovenly, and quite possibly a little ripped most of the time, Kinane deals in resignation, waxing eloquent, for instance, on the sense of defeat one feels on receiving an unsliced Domino’s pizza in error and realizing that one is just going to have to fold the whole thing up like a big “Italian taco” and force it down.
When I saw Kinane at Just for Laughs this summer, he was in heavy futility mode, because if you’re a self-admitted mess—”first-generation white trash,” he says—the happy times are inevitably followed by dark consequences. Kinane plays with and pokes at that irony. 11/15-11/18: Thu and Sun 8 PM, Fri-Sat 8 and 10:30 PM, Up Comedy Club, 230 W. North, 312-662-4562, upcomedyclub.com, $20.