Given a higher profile by her exposure on the Comedians of Comedy tours and documentaries alongside friends Patton Oswalt, Brian Posehn, and Zach Galifianakis, Maria Bamford has moved up a few levels in terms of exposure and general hipness. Luckily, her material has elevated as well. Bamford's first album, The Burning Bridges Tour, overemphasized the comedian's cartoony aspects, most notably a voice that makes her sound like Betty Boop's neurotic sister. That trait is modulated on How to Win, and Bamford's material takes a less insular turn, focusing on more social and political topics in routines like "I Heart My Country" and "Competitive Living." Even her more personal material takes a different shape, including some amusingly dark turns like the hilarious "Sister Sarah," a description of her older sister's work as a pathologist. Or, as Bamford sweetly introduces her, "This is my sister Sarah. She cuts up the dead into chunks." Bamford is a low-key comedian more interested in the wry observation than the manic belly laugh, which makes odd digressions like the tour de force soundtrack of old man body noises in "Dad" all the more surprising and funny.
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AllMusic Review by Stewart Mason