In this 20th Anniversary Special, Live Wire celebrates some of its most memorable moments in the past two decades. Host Luke Burbank gets interviewed by former host Courtenay Hameister about taking the reins of the show and how the embarrassment he felt as a child led to his "openness" onstage; Americana singer-songwriter Charley Crockett chats about busking and train-hopping, before performing "I Wanna Cry" from his album Lonesome as a Shadow; and Moshow the Cat Rapper lives his truth with a rollicking rap "Don't Declaw Your Cat."

Comedian Paul F. Tompkins chats about his improv comedy podcast The Neighborhood Listen, where he and fellow comedians re-enact posts from the app Nextdoor; poet Safiya Sinclair discusses her memoir How to Say Babylon, in which she recounts growing up Rastafarian in Jamaica under the strict patriarchy of her father; and singer-songwriter Isabeau Waia'u Walker performs her song "All My Friends Think I'm Okay." Plus, host Luke Burbank and announcer Elena Passarello share some unhinged behavior from the neighbors of our listeners.

Acclaimed writer Cheryl Strayed (Wild, Tiny Beautiful Things) discusses her new personal essay "Two Women Walk into a Bar," which follows her complicated relationship with her late mother-in-law; stand-up comedian Jay Jurden bridges the generational divide with some poignantly hilarious observations on Boomers and Gen Z; and singer-rapper-poet Dessa performs "Hurricane Party" from her latest album Bury the Lede. Plus, host Luke Burbank and announcer Elena Passarello unpack the benign (but complicated) relationships our listeners have with the people from their everyday lives.

Comedian and writer Aparna Nancherla discusses her memoir Unreliable Narrator and why her mother made her order pizza to combat her shyness; stand-up comedian Gary Gulman riffs on the false notion of dangerous scissors in elementary school; singer-songwriter and historian No-No Boy performs his song "1603," featured on his latest album Empire Electric, which tells the story of the first non-Native sighting of Oregon by a multicultural crew of sailors who fell through the cracks of history. Plus, host Luke Burbank and announcer Elena Passarello learn about the times our listeners suffered from impostor syndrome.

Cartoonist Emily Flake (The New Yorker) reveals Joke in a Box, her 70-card deck of creative prompts, which results in some live cartooning from the stage; writer and artist Tessa Hulls discusses her graphic memoir Feeding Ghosts, which looks at the three generations of Chinese women in her family; and indie pop duo Pure Bathing Culture perform "The Memento" from their latest album Chalice. Plus, host Luke Burbank and announcer Elena Passarello tells us some favorite (short) jokes.

Comedian Gary Gulman (The Great Depresh) discusses his memoir Misfit: Growing Up Awkward in the '80s, his struggles with mental health, and the awkwardness of being recognized in the psyche ward; Oregon Poet Laureate Anis Mojgani reads from his newest collection The Tigers, They Let Me and makes the case for why poetry exists all around us; singer-songwriter Olive Klug touches on the TikTok generation of songwriting, before performing her song "Raining in June." Plus, host Luke Burbank and announcer Elena Passarello share the ways in which our listeners have been unexpectedly cheered up by others.

Comedian and writer Moshe Kasher dives into his new memoir Subculture Vulture, which explores the six communities which shaped his life, from AA and Burning Man to sign language interpretation and his ultra-Hasidic upbringing; stand-up comedian Mohanad Elshieky tells us why he might be the most dangerous man in America; and indie band Glitterbox perform their single "TV." Plus, host Luke Burbank and announcer Elena Passarello chat about some niche subcultures our listeners have belonged to.

Comedian and writer Scott Aukerman brings his wildly popular improv podcast Comedy Bang! Bang! to book form and reveals how a goofy name and an occupation is really how a character begins; astrophysicist Sarafina El-Badry Nance explores her own universe as a woman, scientist, cancer advocate, and one-time swimsuit model in her book Starstruck: A Memoir of Astrophysics and Finding Light in the Dark; rock ensemble and faux cult Family Worship Center perform "Snake Dance" from their new album Kicked Out Of The Garden. Plus, host Luke Burbank and announcer Elena Passarello share the alter egos of some of our listeners.

Bestselling writer Lindy West (Shrill) chats about her new podcast Text Me Back, which unpacks friendship, the news, and text threads; comedian Paul F. Tompkins takes a stab at some other P.F.T. acronyms; and soul ensemble Ural Thomas & The Pain perform "No Distance." Plus, host Luke Burbank and announcer Elena Passarello share some texting habits that really irk our listeners.

Author Héctor Tobar explores the meanings and myths of the term "Latino" in his sixth book Our Migrant Souls; comedian and writer Jena Friedman (Borat Subsequent Moviefilm) chats about her debut collection of essays Not Funny and recounts the time she put her foot in her comedic mouth; and indie folk trio Joseph performs a cover of Tom Waits' song "Come On Up to the House." Plus, host Luke Burbank and announcer Elena Passarello explain why you shouldn't attempt to be as funny as David Sedaris.