In this bonus trip to the Desert Island Jukebox, Jim highlights a singer who spent years in the orbit of some of post-punk's most celebrated and notorious figures before stepping into the spotlight herself. 

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This week, hosts Jim DeRogatis and Greg Kot are joined by returning guest and favorite music writer Jimmy McDonough. Jimmy recently released a biography 40 years in the making, Gary Stewart: I Am From the Honky-Tonks, and joins the show to help Jim and Greg run down five essential tracks from the cult country artist. The hosts also review new albums from Jill Scott, Mandy, Indiana, and Aldous Harding.

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Featured Songs:

Gary Stewart, "Honky Tonk Man," Honky Tonk Man (Single), RCA, 1981

The Beatles, "With A Little Help From My Friends," Sgt. Pepper's Lonely Hearts Club Band, Parlophone, 1967

Jill Scott, "Offadaback," To Whom This May Concern, Blues Babe, 2026

Jill Scott, "Liftin' Me Up," To Whom This May Concern, Blues Babe, 2026

Jill Scott, "Pay U on Tuesday," To Whom This May Concern, Blues Babe, 2026

Mandy, Indiana, "Sevastopol," URGH, Sacred Bones, 2026

Mandy, Indiana, "Magazine," URGH, Sacred Bones, 2026

Mandy, Indiana, "I'll Ask Her," URGH, Sacred Bones, 2026

Aldous Harding, "Venus in the Zinnia," Train On The Island, 4AD, 2026

Aldous Harding, "Train on the Island," Train On The Island, 4AD, 2026

Aldous Harding, "I Ate the Most," Train On The Island, 4AD, 2026

Aldous Harding, "Coats," Train On The Island, 4AD, 2026

Aldous Harding, "One Stop," Train On The Island, 4AD, 2026

Gary Stewart, "Sweet Tater and Cisco," You're Not The Woman You Used To Be, MCA, 1975

Gary Stewart, "Drinkin' Thing," Out of Hand, RCA, 1975

Gary Stewart, "Flat Natural Born Good-Timin' Man," Steppin' Out, RCA, 1976

Gary Stewart, "Pretend I Never Happened," Your Place or Mine, RCA, 1977

Courtney Barnett, "Scotty Says (Live on Sound Opinions)," Sometimes I Sit and Think, and Sometimes I Just Sit, Mom + Pop Music, 2015

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In this bonus Desert Island Jukebox episode, Greg shares a cult favorite from Milwaukee's psychedelic scene.

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This week, hosts Jim DeRogatis and Greg Kot dig into Willie Nelson’s vast catalog of 150+ albums. Along with author Geoffrey Himes, they highlight the “five essential” albums people should hear. They also review the latest album from Kacey Musgraves.

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Featured Songs:

Willie Nelson, "Stardust," Stardust, Columbia, 1978

The Beatles, "With A Little Help From My Friends," Sgt. Pepper's Lonely Hearts Club Band, Parlophone, 1967

Kacey Musgraves, "Dry Spell," Middle of Nowhere, Lost Highway, 2026

Kacey Musgraves, "Middle of Nowhere," Middle of Nowhere, Lost Highway, 2026

Kacey Musgraves, "Horses and Divorces (featuring Miranda Lambert)," Middle of Nowhere, Lost Highway, 2026

Kacey Musgraves, "Uncertain, TX (featuring Willie Nelson)," Middle of Nowhere, Lost Highway, 2026

Willie Nelson, "Blue Eyes Crying in the Rain," Red Headed Stranger, Columbia, 1975

Willie Nelson, "Phases and Stages (Theme) / Washing the Dishes," Phases and Stages, Atlantic, 1974

Willie Nelson, "Bloody Mary Morning," Phases and Stages, Atlantic, 1974

Willie Nelson, "Help Me Make It Through the Night," Sings Kristofferson, Columbia, 1979

Willie Nelson, "Georgia On My Mind," Stardust, Columbia, 1978

Willie Nelson, "I Guess I've Come to Live Here in Your Eyes," Spirit, Island, 1996

Willie Nelson, "On the Road Again (Live)," Live! At The US Festival (June 4, 1983), Shout! Factory, 1983

Willie Nelson, "Last Man Standing," Last Man Standing, Legacy, 2018

Willie Nelson, "Always on My Mind," Always on My Mind, Columbia, 1982

Gary Stewart, "She's Actin' Single (I'm Drinkin' Doubles)," Out of Hand, RCA Victor, 1975

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In this bonus Desert Island Jukebox, Jim pays tribute to legendary American songwriter Chip Taylor, whose pop and country songs were recorded by countless artists— including one of Jim’s favorites, The Troggs. Taylor died on March 23, 2026, at the age of 86.

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This week, hosts Jim DeRogatis and Greg Kot are joined by author Nic Brown for a classic album dissection of the debut from The Violent Femmes. They delve into the unexpected staying power of songs like "Add It Up" and "Blister In The Sun" and Brown shares new insights into the album from his recent interviews with the band members.

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Featured Songs:

Blister In The Sun, "Violent Femmes," Violent Femmes, Slash, 1983

The Beatles, "With A Little Help From My Friends," Sgt. Pepper's Lonely Hearts Club Band, Parlophone, 1967

Please Do Not Go, "Violent Femmes," Violent Femmes, Slash, 1983

Confession, "Violent Femmes," Violent Femmes, Slash, 1983

Kiss Off, "Violent Femmes," Violent Femmes, Slash, 1983

Add It Up, "Violent Femmes," Violent Femmes, Slash, 1983

Gone Daddy Gone, "Violent Femmes," Violent Femmes, Slash, 1983

Good Feeling, "Violent Femmes," Violent Femmes, Slash, 1983

American Music, "Violent Femmes," Why Do Birds Sing, Reprise, 1991

Willie Nelson, "On The Road Again (Live)," Honeysuckle Rose, Columbia, 1980

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This week on the Desert Island Jukebox, Greg cues up a song inspired by outlaw airwaves. It’s a reminder of a time when discovering music still felt like stumbling onto a secret signal.

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This week, hosts Jim DeRogatis and Greg Kot share some of their favorite artists who beat the dreaded sophomore, delivering follow-ups that proved their debuts were no fluke. The hosts will also hear picks from the production staff.

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Featured Songs:

Horsegirl, "Switch Over," Phonetics On and On, Matador, 2025

The Beatles, "With A Little Help From My Friends," Sgt. Pepper's Lonely Hearts Club Band, Parlophone, 1967

Black Sabbath, "Paranoid," Paranoid, Vertigo, 1970

Public Enemy, "Bring the Noise," It Takes A Nation of Millions to Hold Us Back, Def Jam, 1988

Led Zeppelin, "Moby Dick," Led Zeppelin II, Atlantic, 1969

Pixies, "Debaser," Doolittle, 4AD, 1989

black midi, "Slow," Cavalcade, Rough Trade, 2021

Kanye West, "Touch the Sky (feat. Lupe Fiasco)," Late Registration, Roc-A-Fella, 2005

Fiona Apple, "Fast As You Can," When the Pawn..., Epic and Clean Slate, 1999

SZA, "Good Days," SOS, TDA and RCA, 2022

Erykah Badu, "Cleva (feat. Roy Ayers)," Mama's Gun, Motown, 2000

D'Angelo, "Chicken Grease," Voodoo, Virgin, 2000

Phoebe Bridgers, "Savior Complex," Punisher, Dead Oceans, 2020

Van Morrison, "Cyprus Avenue," Astral Weeks, Warner Bros., 1968

Violent Femmes, "Please Do Not Go," Violent Femmes, Slash, 1983

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In this bonus episode, Jim digs up a song that owes more to AM radio nostalgia than to being, well…good.

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This week, hosts Jim DeRogatis and Greg Kot talk with biographer Will Hermes about his book on Lou Reed, as well as Lou’s music, persona, legacy and more.

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Featured Songs:

Lou Reed, "Walk on the Wild Side," Transformer, RCA, 1972

The Beatles, "With A Little Help From My Friends," Sgt. Pepper's Lonely Hearts Club Band, Parlophone, 1967

The Velvet Underground and Nico, "Sunday Morning," The Velvet Underground & Nico, Verve, 1967

The Velvet Underground and Nico, "Heroin," The Velvet Underground & Nico, Verve, 1967

The Velvet Underground, "Pale Blue Eyes," The Velvet Underground, MGM, 1969

Lou Reed, "Coney Island Baby," Coney Island Baby, RCA, 1975

The Velvet Underground, "Some Kinda Love," The Velvet Underground, MGM, 1969

Lou Reed, "How Do You Think It Feels," Berlin, RCA, 1973

Lou Reed, "Perfect Day," Transformer, RCA, 1972

The Velvet Underground, "Sweet Jane," Loaded, Cotillion, 1970

The Velvet Underground and Nico, "I'll Be Your Mirror," The Velvet Underground & Nico, Verve, 1967

The Velvet Underground, "Candy Says," The Velvet Underground, MGM, 1969

Pixies, "Here Comes Your Man," Doolittle, 4AD and Elektra, 1989

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In this bonus episode, Greg shares a song that was championed early on by English radio DJ John Peel.

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