Actor Kal Penn and comedian Dan Soder drop by Ask Me Another's first-ever Tournament of Champions, where we bring back four previous winning contestants to find who will be the big big winner. Penn talks about representing New York City's diversity in his comedy series Sunnyside. Then, he enters the ring to play a wrestling quiz against Soder, who stars in a new HBO special.

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Ophira and Jonathan use the power of trivia to melt the heart of puzzle guru Ebenezer Scrooge. Plus, actor Anthony Ramos (Hamilton, She's Gotta Have It). This episode originally aired Dec. 22, 2017.

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Singer-songwriter and activist Paula Cole shares how jazz inspired her to find her own Grammy-winning sound, and plays games that show off her anatomical and ornithological knowledge. Then, contestants play an audio quiz that reminds them why they should always turn off their cell phones before a show.

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Musician Trace Adkins shares the chance encounter that launched his career, and songwriter Carlene Carter reflects on growing up part of a legendary family. This episode originally aired May 31, 2019.

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At the Aztec Theatre in San Antonio, Texas, Americana singer-songwriter Robert Earl Keen describes how his early days spent in Houston barrooms led to a career in music, how he first met his longtime friend, Lyle Lovett, and why his daughter had to talk him into doing his own podcast. Then he demonstrates one of his superpowers: knowing every U.S. president's birthday. Plus, things get cheesy when contestants play a really gouda music parody game.

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Josh Gondelman, talks about why he gives strangers pep talks on Twitter, and Catherine Cohen explains how she makes her cabaret comedy into fashion. This episode originally aired June 14, 2019.

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Latino punk veteran Alejandro Escovedo talks about growing up in a big musical family, his year living in the Chelsea Hotel, and his latest album, The Crossing. Then, his love of surfing and French cinema is tested in a gnarly game of This, That, or the Other. Plus, contestants channel their inner fifth grader in a game where every answer can be spelled upside-down on an LCD calculator.

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Ask Me Another heads to Seattle! Comedian and host of Nailed It!, Nicole Byer reflects on how she went from waiting tables to performing stand-up, and why celebrating failure is important. This episode originally aired on June 28, 2019.

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At the Lobero Theatre in Santa Barbara, Grammy Award-winning singer-songwriter and "yacht rock" pioneer Michael McDonald reflects on his father's disappointment when he put down the banjo for rock and roll, and why he still considers himself a Doobie Brother. Then he plays a game inspired by his love of singers from the 1960s and '70s. Plus, meet the captain of a "cute lil' yellow tugboat," and gain some nautical knowledge.

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Taylor Schilling explains why after seven seasons on Orange Is the New Black, she's going to clown school. This episode originally aired May 10, 2019.

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