Sad Song Queens

In this episode of Sad Song Queens, hosts Laura Webb and Lindsay Wolfington sit down with Grammy-winning songwriter, producer, and Semisonic frontman Dan Wilson to unpack one of the most quietly devastating songs in his catalog: "Fly Safe." For a podcast built around the songs that make people cry, Dan turns out to be the perfect guest — a self-described "earnest" songwriter whose melodies, he admits, sound sad even when he's trying to write something hopeful.

Dan Wilson is a Minneapolis-born, Los Angeles-based artist with four Grammy wins across seven nominations, including Song of the Year for the Chicks' "Not Ready to Make Nice," Album of the Year as producer on Adele's 21, Best Country Song for Chris Stapleton's "White Horse," and Best Song Written for Visual Media for "It Never Went Away" with Jon Batiste. As the frontman of Semisonic, he also co-wrote generation-defining hits like "Closing Time" and "Secret Smile."  This episode's conversation focuses on "Fly Safe," a song many fans read as purely comforting, and which Dan reveals is anything but simple underneath the surface.

Laura and Lindsay walk through their own theories of the song — pointing out that lyrically, "Fly Safe" reads like reassurance: get high, travel light, think about the good times, we can start again.  Dan agrees, and then goes further, explaining that the phrase "fly safe" itself carries an inherent unease — you only say it to someone you love, and only because there's a real chance something could go wrong.

That tension, it turns out, wasn't accidental. Dan opens up about the real circumstances behind the song: he wrote it during a genuinely difficult period in his marriage when he and his wife were both preparing to leave for separate trips, and the phrase "fly safe" became loaded with everything neither of them was saying out loud. Dan describes the uncertainty of the lyric — a hope that they'd find their way back to each other.  

They then discuss the songwriting process, and true to what he calls his "Nashville habit," Dan says the title came before anything else.  He explains the song's minor-to-relative-major chord movement, and why it never fully resolves — a trick he credits to years of working with producer Rick Rubin, who trained him to take the "easy, sweet resolves" out of his chord progressions.  The result is a song that ends on a minor chord after a swelling, hopeful instrumental section — leaving listeners suspended between reassurance and doubt, which is exactly the emotional trick that makes "Fly Safe" so effective as a sad song.  

The episode also touches on his history with Semisonic, including how their label initially rejected their album Feeling Strangely Fine outright before offering the band money to re-record it — a moment that was talked down by his longtime manager, Jim Grant, who convinced him not to touch songs like "Closing Time" and "Secret Smile." 

Toward the end of the episode, Dan shares what's next for him, including Semisonic's new single "Don't Give Up Yet," written as a love letter to Minneapolis. He explains how the song began as an unfinished tribute to bassist John after John suffered a stroke that initially took away his ability to play — and how Dan eventually finished the lyrics under very different, heavier circumstances tied to his hometown. A recent Semisonic performance in front of over 35,000 people in the Twin Cities, was made even more meaningful by John's return to the stage, relearning bass with a pick after his stroke.

This episode is a must-listen for fans of Dan Wilson, Semisonic, Adele, and anyone who has ever choked up over a song that sounds happier than it feels. 

Don't miss part two of this conversation with Dan Wilson next week, where we go deep into the making of Adele's "Someone Like You," plus Dan Wilson's definitive, handwritten list of the saddest songs of all time.

Topics covered: Dan Wilson, Fly Safe, Semisonic, Minneapolis, Adele Someone Like You, Sad Song Queens
Support the show
To help support these artists’ as well as their favorite sad songs, please check out our Official Spotify Playlist! 
Find us elsewhere: 
https://linktr.ee/sadsongqueens

If you like what you hear, you can buy us a coffee!
Our theme song is "All My Favorite Songs" by Weezer, courtesy of Crush Music, Atlantic Recording Company, and WEA International Inc, a Warner Music Company.
Our Sad Song Queen image was created by Keahu Kahuanui. 
Check out our friends at The Songwriting School of Los Angeles!

Music supervisors Laura Webb and Lindsay Wolfington kick off this episode with a summer catch up. From travel tales and rock biographies to the tracks on heavy rotation, the Sad Song Queens sync up on everything that defined their summer break.

The duo peels back the curtain on the raw realities of music supervision and clearance, and music coordinator Jordan Linsley steps into the studio to talk shop—and host a high-stakes, hilarious game of Misunderstood Songs.

Play along as Laura and Lindsay throw down, attempting to decode famously botched lines from your favorite bands. Equal parts industry insider track and laugh-out-loud song trivia, this is the ultimate listen for music lovers and trivia nerds alike. Stick around to the very end to see who takes the crown!
Support the show
To help support these artists’ as well as their favorite sad songs, please check out our Official Spotify Playlist! 
Find us elsewhere: 
https://linktr.ee/sadsongqueens

If you like what you hear, you can buy us a coffee!
Our theme song is "All My Favorite Songs" by Weezer, courtesy of Crush Music, Atlantic Recording Company, and WEA International Inc, a Warner Music Company.
Our Sad Song Queen image was created by Keahu Kahuanui. 
Check out our friends at The Songwriting School of Los Angeles!

New York rock veteran Jesse Malin joins Sad Song Queens hosts Laura Webb and Lindsay Wolfington to break down "My Little Life," a song that's taken on an entirely new meaning after the health crisis that nearly ended his career. Malin has spent more than two decades as one of New York's most beloved rock artists — his 2003 solo debut The Fine Art of Self-Destruction earned him praise from Rolling Stone, and his songs have since been covered by Bruce Springsteen, Lucinda Williams, Green Day, Elvis Costello, Bleachers, and Counting Crows. In 2023, Malin suffered a rare spinal stroke that left him paralyzed from the waist down. Rather than step out of the spotlight, he learned to stand again and returned to the stage the following year, later channeling the experience into his off-Broadway debut, Silver Manhattan, a Drama Desk–nominated autobiographical production, and his new memoir, Almost Grown: A New York Memoir.

"My Little Life" plays a pivotal role in Silver Manhattan, and the hosts open by unpacking why the song — written years before Malin's stroke — feels almost prophetic now. Malin explains that he originally wrote it about people in his life who struggled with the simplest, everyday things: friends and family members who felt like they never quite fit in, for whom just getting through the day carried real weight. 

The conversation moves into how "My Little Life" ended up in Silver Manhattan in the first place. Malin describes handing his entire back catalog over to the play's director and co-writer to cherry-pick from, and being genuinely surprised by some of their choices — only to find that hearing his own songs performed in a new context, in front of an audience, changed how he understood them. He's candid about the physical challenge of performing at all after his stroke, describing the months of physical therapy it took just to stand and balance long enough to sing one song upright for his sold-out Beacon Theater shows.

Malin also opens up about the origins of Silver Manhattan itself — conceived the day after that Beacon Theater show, when a friend suggested he turn his catalog and his story into an ongoing New York residency rather than retreat. What started as that idea grew into a 92-minute rock show built with his full band, tracing his life from his old hardcore band Heart Attack and his punk band D Generation through his solo career, while also functioning, in his words, as a love letter to Manhattan and to the freewheeling, walking-the-streets life he lost and then had to rediscover from a wheelchair.

Elsewhere in the episode, Malin talks about writing "Shane," a song named for his friend and hero Shane McGowan of the Pogues, and how singing that song live took on new weight after McGowan's death, and after Malin himself began touring in a wheelchair. He and the hosts also dig into Malin's reflections on chasing music before the internet made it instantly accessible,  his teenage years in the New York hardcore and punk scenes and its DIY attitude, and how PMA became a guiding life mantra. Don’t miss this candid and reflective conversation between the Sad Song Queens and a New York music legend.
Support the show
To help support these artists’ as well as their favorite sad songs, please check out our Official Spotify Playlist! 
Find us elsewhere: 
https://linktr.ee/sadsongqueens

If you like what you hear, you can buy us a coffee!
Our theme song is "All My Favorite Songs" by Weezer, courtesy of Crush Music, Atlantic Recording Company, and WEA International Inc, a Warner Music Company.
Our Sad Song Queen image was created by Keahu Kahuanui. 
Check out our friends at The Songwriting School of Los Angeles!

Grammy-winning, Tony- and Emmy-nominated singer-songwriter Sara Bareilles joins Sad Song Queens hosts Laura Webb and Lindsay Wolfington for one of the most emotionally raw conversations the podcast has ever recorded. The episode centers on “Forever,” the penultimate track from Bareilles’ seventh studio album, Good Grief, released August 28th — a record built entirely around loss, memory, and the power of music to heal. 
Sara Bareilles broke through in 2007 with “Love Song,” pushing her platinum debut Little Voice into the Billboard 200’s top ten, and later composed the music and lyrics for Broadway’s Waitress, earning a Tony nomination before also performing in the show and in the 2022 revival of Into the Woods. The making of Good Grief was documented in the film Sara Bareilles: Good Grief, which premiered at Tribeca before moving into theaters — companion viewing the hosts reference throughout the episode.
At the center of the conversation is the origin story of “Forever” itself, a discussion which brings all 3 ladies to tears. Bareilles details how the song developed over time, initially written while grappling with two overlapping losses in 2020. The song sat unfinished until Bareilles’ close friend and Waitress co-star Gavin Creel was later diagnosed with the illness that eventually took his life, and she reshaped the song with him in mind. By the end, she says, it had absorbed multiple losses, including her own experience with infertility.
The episode also digs into the song’s winding production and Sara’s experience claiming production ownership on this record for the first time in her career, after years of having her demos routinely replaced in the studio.
Grief itself is the philosophical backbone of the conversation. Bareilles reframes it not as something to fix, but as proof of enduring love, drawing on a conversation with poet Andrea Gibson about how the people we lose live on through the people who loved them. Host Laura Webb shares her own experience of ambiguous loss watching her father live with Alzheimer’s, and she and Bareilles connect on “signs” they receive from loved ones and what helps them move through loss. Sara also discusses the upcoming Good Grief Tour — her first since 2019 — and the fan voicemail project she launched alongside it, inviting listeners to share their own stories of loss.
Beyond “Forever,” the episode traces melancholy as a throughline across Bareilles’ catalog, reflecting on earlier songs like “Gravity” and “Manhattan” to this new album, and how her songwriting has widened over time from romantic breakups to the many other ways people leave each other. Whether you’re a longtime fan, a Good Grief documentary viewer, a songwriter curious about her process, or someone processing your own grief, this is an unusually candid look at how Bareilles turns loss into something you can hold onto. Grab those tissues for a good cry with Sara Bareilles and the Sad Song Queens.
Support the show
To help support these artists’ as well as their favorite sad songs, please check out our Official Spotify Playlist! 
Find us elsewhere: 
https://linktr.ee/sadsongqueens

If you like what you hear, you can buy us a coffee!
Our theme song is "All My Favorite Songs" by Weezer, courtesy of Crush Music, Atlantic Recording Company, and WEA International Inc, a Warner Music Company.
Our Sad Song Queen image was created by Keahu Kahuanui. 
Check out our friends at The Songwriting School of Los Angeles!

My Morning Jacket frontman Jim James joins Laura Webb and Lindsay Wolfington to unpack “Get The Point,” a beautiful and sincere breakup song from the 2015 album, The Waterfall. Recorded in a cliffside Stinson Beach studio, the track was written during the collapse of a relationship James describes as an “unbelievable cosmic love” tangled up with active alcoholism and self-hatred.

Jim opens up about writing from inside the fog of addiction, learning to trust his own truth over someone else’s, and why his favorite songs — like his own — are always “sad yet hopeful.” He also gets candid about sobriety, mental health, and why musicians talking openly about struggle matters more than ever.

The conversation lands just ahead of Wowed Out, James’s first solo album in eight years, dropping August 28. Expect deep-dive musicianship talk (that pedal steel!), reflections about the universe, music and Kermit the Frog, and one of the most honest discussions of a breakup song you’ll hear this year.
Support the show
To help support these artists’ as well as their favorite sad songs, please check out our Official Spotify Playlist! 
Find us elsewhere: 
https://linktr.ee/sadsongqueens

If you like what you hear, you can buy us a coffee!
Our theme song is "All My Favorite Songs" by Weezer, courtesy of Crush Music, Atlantic Recording Company, and WEA International Inc, a Warner Music Company.
Our Sad Song Queen image was created by Keahu Kahuanui. 
Check out our friends at The Songwriting School of Los Angeles!