Album Swap: 'Autobiography' by Ashlee Simpson and 'Not a Pretty Girl' by Ani DiFranco

Key takeaways

• The SNL incident that capsized Ashlee Simpson's career was bad luck compounded by bad timing. During her October 2004 appearance, a drummer hit the wrong button and triggered the vocal track for "Pieces of Me" while the band had started playing "Autobiography." Ashlee did the now-infamous jig and walked offstage. The damage was extreme partly because SNL happened to be filming a behind-the-scenes documentary that week, flooding the aftermath with footage. Critically, she had lost her voice before the show and was filmed crying in rehearsals — the backing track was a necessity, not fraud. The public treated it as Milli Vanilli anyway.

• The SNL moment accidentally sparked a mainstream conversation about rockism. A New York Times essay followed shortly after, asking general readers whether rock-era authenticity standards should apply to pop artists with different goals. Nora argues that the world where Taylor Swift, Sabrina Carpenter, and Olivia Rodrigo are taken seriously as complete artists is, in some ways, a world Ashlee's disaster helped catalyze. Nathan adds the post-Napster layer: a shakier recording industry pushed labels hard toward name-recognition bets, making "industry plant" accusations far more common and the SNL moment far more damaging.

• _Autobiography_ is a polished album with one great song and several indefensible ones. "Pieces of Me," produced by John Shanks, has over 100 million Spotify streams; the next track from the same album, "La La," sits at 19 million. Nathan hears borrowed DNA throughout—"Unreachable" lifts the piano chords from Fiona Apple's "Criminal," "Undiscovered" stacks U2's "With or Without You" and "Bad" on top of each other, "Love Makes the World Go Round" echoes Jimmy Eat World's "The Middle." The album is passable, he says. It just cannot beat the allegations.

• Ani DiFranco built the template for artist independence that the industry still references. She emancipated herself from her mother at 15, came out as openly queer early in her career, and released every one of her 21 albums on her own Buffalo-based label, Righteous Babe Records, turning down every major label offer. She distributed CDs through the mail and independent stores until signing a limited distribution deal around this album. Prince recognized her as a kindred spirit and they collaborated across each other's records. Nathan credits her influence on singer-songwriters from Phoebe Bridgers to Taylor Swift.

• DiFranco's guitar playing is the overlooked half of her artistry. She taped Lee Press-On nails to her fingers with electrical tape to generate enough percussive force to carry bass on an acoustic guitar, because she usually performed solo with no bass player. She played in drop-D and other non-standard tunings and used her breath as percussion. Nathan compares her to Joni Mitchell as a guitarist whose technique is routinely overshadowed by her reputation as a lyricist. His favorite track from Not a Pretty Girl is "32 Flavors," a six-minute-plus song he calls a light-yourself-on-fire moment; Nora highlights "Worthy," "Shy," and "Sorry I Am."

• The Alana Davis cover of "32 Flavors" introduced the song widely but stung DiFranco. Davis changed some of the lyrics and the recording ended up in an NFL ad, reaching an audience DiFranco had deliberately chosen not to court. Nathan calls it bittersweet: the cover showed people how powerful the song was, but it did exactly what DiFranco had spent her whole career refusing to do — commercialize her work through channels she'd avoided on principle. Her original is better, he says, which makes the whole situation worse.

People, organizations, products, and links mentioned

• Ashlee Simpson — pop-rock artist; Autobiography (2004); won Season 14 of The Masked Singer as "Galaxy Girl"
• Ani DiFranco — singer-songwriter; Not a Pretty Girl (1995)
• Nora Princiotti and Nathan Hubbard — hosts
• Kaia McMullen — producer
• Jessica Simpson — Ashlee's sister; Newlyweds reality show; formerly dated Tony Romo; married Nick Lachey
• Pete Wentz — Ashlee's ex-husband (Fall Out Boy)
• Evan Ross — Ashlee's current husband; Diana Ross's son
• John Shanks — producer of Autobiography; also produced Kelly Clarkson's "Breakaway," Hilary Duff's "Fly," Sheryl Crow's "The First Cut Is the Deepest," Alanis Morissette's "So-Called Chaos," Robbie Robertson's "Shine Your Light"; won Grammy for Best Producer
• Kara DioGuardi — songwriter; wrote several songs on Autobiography; former American Idol judge
• Alana Davis — covered "32 Flavors"
• Andy Stochansky — Canadian drummer on Not a Pretty Girl
• Prince — collaborated with Ani DiFranco across their respective albums
• Taylor Swift, Phoebe Bridgers — cited as artists influenced by DiFranco
• Michelle Branch — referenced from prior album swap episode
• Avril Lavigne, Britney Spears, Olivia Rodrigo, Sabrina Carpenter, Kelly Clarkson, Katy Perry — mentioned in comparison
• Joni Mitchell — cited as a comparably underrated guitarist
• John Mayer — mentioned as another performer whose live talent is immediately clarifying
• Lady Gaga — referenced via an American Idol performance anecdote
• Dave Chappelle — compared to DiFranco for publicly fighting ownership of his creative work
• Dave Matthews Band — compared to DiFranco's tape-trading grassroots fanbase model
• Louis Capaldi — mentioned as a recent example of a performer whose backing tracks failed live
• Rudy Giuliani, Ken Jeong, Robin Thicke — mentioned in Masked Singer discussion
• Righteous Babe Records — DiFranco's independent label, based in Buffalo
• Out of Range (Ani DiFranco) — Nathan's pick for her best album; includes "You Had Time"
• Hadestown — Broadway musical; DiFranco contributed
• The Masked Singer (Fox) — Ashlee Simpson won Season 14
• New York Times rockism essay — published in the aftermath of the SNL incident
• Lilith Fair — mentioned as context for mid-90s female singer-songwriters

Notable moments

• Nathan keeps correcting Nora for calling her fiancé her "fiancé" — since the episode was recorded before the wedding but releases after. She refuses to pre-call him her husband ("incredibly bad juju") and settles on Bobby.
• Nathan reveals he once encored "Pieces of Me" with his band, alongside "Toxic" and "Genie in a Bottle." Nora immediately names it "geese covering baby before it was cool" and demands audio evidence.
• On the album pairing: Nora says Nathan chose Not a Pretty Girl like a wine pairing — "You knew my entree choice and you were a musical sommelier." Nathan: "1,000%. Thank you for recognizing that."
• Nathan on "La La": "I'm like an alley cat, drink the milk up, I want more." He's appalled. He's also separately annoyed that Ashlee — whose sister famously didn't know what "Chicken of the Sea" was — uses the British spelling "aeroplane" in the same song.
• Nora on watching the SNL incident: "My whole GI system turned itself into a pretzel just watching this poor woman have just this national moment of shame."
• Nathan on why seeing Ani DiFranco live made him quit music: "She's one of the people who convinced me that I needed to stop playing because I just wasn't good enough... you see someone like that and you're like, okay, that is what an artist ought to be."
• Nathan on the Alana Davis cover: "If you're on Ani DiFranco Island, you don't want somebody else taking it" — and then adds that Davis changed some of the lyrics, which upset DiFranco, and DiFranco's version is better anyway.

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