Aimee Mann’s Best Comedy Crossover Moments

Before deciding on a title for her new album, Aimee Mann told a friend that her record was full of her “usual songs about mental illness.” Mann, whose songs often delve into life’s melancholies, began to see the humor in another friend’s suggestion that she call the album Mental Illness. “It’s so bald, but also accurate and funny, so it really made me laugh,” Mann said. “And I felt like if it’s making you laugh, there must be something accurate about it.”

While Mann is known for her songwriting abilities, skillful enough to inspire director Paul Thomas Anderson to write Magnolia, she is also an avid comedy fan. “A lot of my friends are comedians, and they’re the most disturbed, saddest, most melancholy creatures,” she recently told Consequence of Sound. Mann has been crossing into the comedy world for over two decades, acting in The Big Lebowski, co-hosting an episode of Comedy Bang Bang with Scott Aukerman, doing guest spots on shows like Portlandia and @midnight, and having her comedian friends act alongside her in music videos.

Mann said of the crossover between comedy and music:

I don’t think that I have lines in my songs that are overtly funny, but they’re lines that make me laugh where it’s funny because it is true, but it’s blunt, like the title Mental Illness. That is so blunt that it’s kind of funny. It’s probably only funny to me, but there’s an element where the intersection with comedy comes in. When it comes to comedians, it’s their use of language, their specific choice of words and the arrangement of words. It’s very musical. Jokes might not work if you put certain words at the front of the sentence rather than the back. That’s fascinating, and I really admire that. That they can do that on the spot without music is really impressive to me.

Here are some Mann’s best crossover moments:

1. Music Video Cameos

Labrador” - Jon Hamm plays director Tom Scharpling (the real Tom Scharpling directed the video, with comedy partner Jon Wurster playing the egotistical leading man), who tricks Mann into doing a shot-for-shot remake of “Voices Carry.” Mann insists she had “no choice” in making the video.

“Charmer” - John Hodgman meets Mann for brunch and recommends she purchase a robot double (Laura Linney) to relieve her from her grueling touring schedule. It works, until the double takes control of Mann’s life, including her friendship with Hodgman.

31 Today” - Morgan Murphy tries to get Mann to laugh using a fake mustache and a cat.  

Soon Enough” - Tim Heidecker (who co-wrote this song with Mann) heads an “innovative intervention.” Bonus: Nathan Fielder directed the video and plays the cameraman who loves Heidecker’s guitar solo.

“I’m Cured” - In her video for “I’m Cured,” Mann dresses as a germ, singing sternly as David Wain and Dave Foley play scientists experimenting ways to cure the common cold. The song was written by Stephen Levinson and his brother Joel along with former Daily Show writer, Rob Kutner. “When we wrote this song for her, we thought, ‘How can we use that ability for evil?’” Levinson said.

2. The Big Lebowski Cameo

Mann popped up in the Coen brothers’ classic film as a nine-toed German nihilist, alongside fellow musician Flea. She only had a few lines and they were in German. She told the The A.V. Club:

Well, I’m supposed to be German, and me and the other Germans are sitting around the diner talking. One of the other guys actually was German, so he and I got together and actually figured out a little dialogue in German so we’d actually have something to say, because otherwise, when they say “action,” you have to make up some fakey German-y fake language. Which is what Flea did, and the other guy is Swedish, so he kind of spoke this Swedish-German composite. He didn’t care.

3. Portlandia Appearance

Playing Fred Armisen and Carrie Brownstein’s cleaning lady, Mann insists that she has to get back to work. They apologize for downloading all of her music.

4. “Come Sail Away” Community Cover

Donald Glover’s farewell episode features a perfectly placed callback to season 1 of the show. In “Debate 109” Troy asks, “Why am I crying? Will I accidentally listen to ‘Come Sail Away’ by Styx again?”  So as Troy says goodbye to the group and prepares to set sail with LeVar Burton (on the aptly named Childish Tycoon), Aimee Mann’s “Come Sail Away” cover sets the bittersweet tone.  

5. @midnight Appearance

Mann went up against Nick Offerman and Dana Gould on the late night show, playing “Name That Tube,” at one point using the word, “glory-hole-lujah.”

6. Lincoln Chafee 1% Promotion on Conan

Lincoln Chafee, the 2016 presidential candidate who gained fame for telling Anderson Cooper he was “being a little rough” on him during a debate, was once polling at 0% in voting polls. Conan O’Brien wanted to get Chafee to 1% so he recruited Mann to sing an energizing campaign song. One of the lines of the song says Chafee “looks like Chris Matthews on a juice cleanse.”

7. Aimee Mann vs. Paul F. Tompkins:

Mann appeared with Tompkins on a live radio show, competing in a game called “Clash of the Hollywood Weirdo Titans.” Tompkins had to come up with synopses based on non-existent movie titles while Mann would create the opening themes.

Titles include The Thumpening and The Guy with the Hat Who Did the Thing.

8. Christmas Trilogy

Mann looks to assemble a pack of celebrities for her Christmas special. She sings to John Krasinski, makes Patton Oswalt fight with Weird Al, deals with a contemptuous Ben Stiller, and encounters a sad Will Ferrell who thinks he’s speaking with Jewel.

9. Andy Kindler Helps Mann Audition SNL Band Hopefuls

Mann and Kindler play two strict judges in a sketch featuring comic DC Pierson. But they don’t want him to play music, instead they want to see what he looks like laughing on TV and if he can sway well to music, but without dancing.

*Bonus: Aimee Mann’s Christmas Carol:

Aimee Mann’s Best Comedy Crossover Moments