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.

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.

Emmy and Tony Award-winner Kristin Chenoweth joins Ask Me Another in Houston, Texas. She reflects on her Wicked-ly impressive career on stage and her latest album, For The Girls. Then, the Broadway star belts it out in a game where she sings the titles of famous musicals, and takes on a quiz inspired by her love of 7-Eleven Slurpees. Plus, a final round with a "BIG" surprise ending.

Ask Me Another hits the road! Matthew McConaughey chats about his love for Austin, Texas and his new role as the University of Texas' Minister of Culture. Then, he reflects on why he still loves the first three words he said on screen, and he's challenged on unusual laws in Texas and some college mascot history.

Ilfenesh Hadera, from the 2017 reboots of Baywatch and She's Gotta Have It, chats about growing up in Harlem, working with Spike Lee, and her new Epix series, Godfather Of Harlem. Then, this DJ school dropout plays a game about hip-hop samples. Plus, contestants play games about old-timey inventions and cheese, and the beloved Fact ag is back!

SNL writer Julio Torres explains the inspiration behind his bilingual series, HBO's Los Espookys, and the El Salvador-meets-New York connection of his comedy special, My Favorite Shapes, which involves strange objects on a conveyor belt. Then, he's challenged to a game where Greek gods are cast as contestants on The Bachelor.