Sad Song Queens

In this episode of the Sad Song Queens, music supervisors Laura Webb and Lindsay Wolfington sit down with the incomparable Brandi Carlile—an Oscar nominee, 11-time Grammy winner, two-time Emmy winner, and New York Times best-selling author who has released ten studio albums to date.  They discuss Brandi Carlile’s stunning new deluxe release, Returning To Myself (Sad Gay Version),  which features intimate, reimagined versions of all ten songs from the original album. Brandi details the meticulous and vulnerable choices behind reshaping these tracks, including a deep-dive discussion into Brandi’s latest single "Human (Sad Gay Version)," her beautiful collaboration with Jon Hopkins. 
Fresh off winning Song of the Year at the 2026 Americana Awards for the title track "Returning To Myself" from her acclaimed 2025 album of the same name, Brandi Carlile joins the show to discuss her incredible career and collaborations with idols like Joni Mitchell and Elton John. She also reflects on how the music she listened to in her adolescence influenced both versions of Returning to Myself, and what sad songs got her through her younger years. 
Laura, Lindsay and Brandi share their love for sad songs and go through many of their favorites to determine what makes a song “sad gay” - a genre in and of itself, according to Brandi - while playing a game of "Sad vs Sad Gay,”  They also share stories about the shows’ past guests whom she has been inspired by and worked with, including Sara Bareilles, Bernie Taupin, the Secret Sisters, and Lucius, celebrating the tight-knit community of incredible artists she continually champions.
Whether you are looking for a good cry, a deep dive into the craft of songwriting, or simply an inspiring conversation about community and creativity, this episode has it all. Grab your tissues, check out the show notes for the full playlist of every track discussed, and tune in now to experience this unforgettable chat with Brandi Carlile!
Keywords: Brandi Carlile, Returning To Myself Sad Gay Version, Human featuring Jon Hopkins (Sad Gay Version), story behind the song, indie folk music, singer-songwriter interviews, music supervision, acoustic sad songs, music supervisor podcast, Lindsay Wolfington, Laura Webb, Sad Song Queens podcast
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!

Singer-songwriter duo, The Secret Sisters, join Sad Song Queens hosts Laura Webb and Lindsay Wolfington to dive into the emotional backstory behind their poignant track, “Hold You Dear” from their 2020 album Saturn Return.  In this intimate conversation, real-life sisters Laura Rogers and Lydia Slagle, reflect on the raw vulnerability of early motherhood, family, and the fleeting nature of time that inspired the song.   

Known for their close vocal harmonies, traditional Southern roots, and introspective songwriting across country, folk, and Americana music, The Secret Sisters have carved out a unique space in modern roots music.  They share details of their music career journey that started unexpectedly when a spontaneously open audition in Nashville led to a record deal and their 2010 self-titled debut, produced by T-Bone Burnett and Dave Cobb. The album brought rapid national attention and tour slots alongside Paul Simon, Willie Nelson, and Ray LaMontagne.   
The Secret Sisters tell Lindsay and Laura about their challenging experiences in the music industry, and how they almost left the business before Brandi Carlile encouraged them to continue making music. Carlile then co-produced two of their albums, You Don't Own Me Anymore (2017) and Saturn Return (2020) - both earning them Grammy nominations for Best Folk Album.  Their most recent album, Mind, Man, Medicine (2024), is a deeply emotional exploration of human connection, self-reliance, and post-pandemic healing co-produced alongside Ben Tanner (Alabama Shakes, St. Paul & the Broken Bones) and John Paul White (formerly of Grammy-winning duo the Civil Wars).   

To wrap up the episode, Laura and Lydia break down their personal favorite cry-worthy tracks from legends like John Prine and George Jones to modern masters like Big Thief and Madison Cunningham, making this an essential listen for anyone who loves a good cry. 

So grab your tissues and prepare for tears as you dive into this deeply moving episode!
Keywords: The Secret Sisters interview, Hold You Dear, Laura Rogers, Lydia Slagle, Cry-worthy songs, songs about motherhood, acoustic folk harmonies, Sad songs podcast, music supervisor podcast, Lindsay Wolfington, Laura Webb

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!

In this episode of Sad Song Queens, hosts Laura Webb and Lindsay Wolfington sit down with Andrew Bird—Grammy-nominated singer-songwriter, violinist, whistler, and recent Emmy winner for Outstanding Original Music and Lyrics. Recorded prior to his big win, this conversation dives into the award-winning track "Need Someone," co-written with composer Gavin Brivik for HBO Max's hit medical drama The Pitt.
Whether you are a longtime fan of Andrew Bird, an admirer of his work across film and television, or simply a lover of deeply emotional, melancholy music, this episode offers a captivating look into his creative process and collaboration with The Pitt composer Gavin Brivik. During the interview, Andrew reveals that he wrote "Need Someone" in just an hour and a half after watching a single poignant scene. He reflects on how writing to picture provided a refreshing constraint, pushing him to be far more emotionally direct than on his solo albums. He also breaks down the song's core theme: the universal human need for connection and comfort during end-of-life care, and the profound reality that healthcare workers are often the last people by our side.
Beyond his 18 studio albums and contributions to projects like The Bear, Ted Lasso, and Disney's The Muppets, Andrew Bird touches on scoring Netflix's upcoming series Pride and Prejudice. He also opens up about his broader artistic philosophy—how fatherhood alleviated his career anxieties, why playing guitar keeps his songwriting grounded compared to complex violin arrangements, the real story behind his iconic whistling, and why live performance offers a far deeper connection than studio recording. To wrap up, Andrew shares some of his personal favorite sad songs and what makes his musical style so unique.
Grab your tissues, tune in, and enjoy this deep dive into music, emotion, and storytelling!
Keywords: Andrew Bird interview, Andrew Bird Emmy, Need Someone Andrew Bird, The Pitt, Gavin Brivik, Emmy-winning song, whistling, Sad songs podcast, music supervisor podcast

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 songwriter Dan Wilson (Semisonic, "Closing Time") returns for part two of his Sad Song Queens interview with hosts and award-winning music supervisors Laura Webb and Lindsay Wolfington.  In this episode, he goes deep on co-writing Adele's heartbreaking hit "Someone Like You." Dan shares the untold story behind the song's iconic piano part, how Adele's iconic “screechy” falsetto note almost got cut, why her mum's tears convinced them to finish the song, and what really happened in the studio during those two legendary writing days.

Plus: Dan breaks down his personal (comprehensive) list of the saddest songs ever written — from "Fast Car" and "Somewhere" to "Rainbow Connection" and "I Can't Make You Love Me" — and explores why nostalgic songs like "In My Life" and "Night Swimming" hit just as hard as the openly heartbreaking ones. 

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 is a must-listen for fans of Dan Wilson, Semisonic, Adele, and lovers of iconic sad songs.

Topics covered: Adele songwriting process, appoggiatura in sad songs, Someone Like You, Saddest songs of all time, Dan Wilson interview, Music production stories, Grammy-winning songwriters.
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!

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!