Aimee Mann, the Oscar-nominated songstress of "Save Me" from the "Magnolia" soundtrack, brings a specific and cutting humor to everything she does. She's both sarcastic and damning, deadpan and sensitive. And her videos -- which have featured the likes of Jon Hamm, Laura Linney, Morgan Murphy, and now her newest duet partner Ted Leo -- are hilarious in their droll weirdness. It's a wacky but understated humor comparable to the IFC series "Portlandia," which actually once featured Mann in a hysterical cameo role.

The 'Til Tuesday vet has always been a fan of comedians; she's had acts like Patton Oswalt and Paul F. Tompkins join her in concert, and she often features funny folks in her music videos. In "Aimee Mann's Christmas Carol," she ran into John Krasinski, Michael Cera, and John C. Reilly.

Mann's newest video "Milwaukee," the first single off the new album she and Ted Leo are releasing as an act called The Both, gives us lots of Leo as a be-denimed loser and plenty of Mann's withering stares.

"Labrador" serves up Jon Hamm as a hotshot director with a devastating mustache, but the real star is Mann, who reenacts her classic video for "Voices Carry" from her 'Til Tuesday days.

Who should play the role of Aimee Mann in a biopic? "Charmer" proves it should probably be Laura Linney.

"Soon Enough" is an intervention gone terribly wrong, and its contempt for phony TV earnestness feels like a classic Mann sentiment. Actually, I bet Michael Stipe would love this video too. His resentments are similar.

"31 Today" is a nutty vid that gives us comedian Morgan Murphy at her most impish. Weirdest thing about it? It's directed by none other than Bobcat Goldthwait.