1. Bob Dylan, Blood On The Tracks
Standout tracks: “Buckets Of Rain”, “If You See Her, Say Hello”
Of course. The record against which all other breakup albums are measured, this Everest of Emo contains all the components of a great breakup story: finding love (“Simple Twist of Fate”), hating your lover (“Idiot Wind”), losing said lover (“You’re Gonna Make Me Lonesome When You Go”), musing on lost love (“If You See Her, Say Hello”), and finally coming to terms with it (“Buckets of Rain”). Great breakup albums guide us through hard times because of their power to give voice to our heartache. In this one, the best songwriter of the modern age sets the stage for all great breakup albums to follow.
2. Josh Rouse, Nashville
Standout tracks: “Street Lights”, “Carolina”
He isn’t as ubiquitous as Jason Mraz or Jack Johnson, but for sheer pop bliss I’ll take Josh Rouse, one of my all-time favorite singer-songwriters. His voice sounds like a less depressive Jeff Tweedy, and his lyrics range from the whimsical to the heartbreaking. The production is glossy but still soulful (not an easy feat), and the string arrangements and horn sections lift the melancholy to grandiosity. Its warmth just envelops you.
3. Bruce Springsteen, Tunnel of Love
Standout tracks: “Two Faces”, “Brilliant Disguise”
One of Bruce’s most underrated albums, this chronicle of his ill-fated marriage to model Julianne Phillips is also one of his most revealing and personal. After the mega hit Born In The U.S.A., the Boss turns his perceptive eye on marriage and commitment. “Nobody knows, baby, where love goes,” he sings, “But when it goes, it’s gone, gone, gone.” It’s his Nebraska for the bedroom: the death of love told stark, cold, and matter-of-fact. This is music about love for adults.
4. Weezer, Pinkerton
Standout tracks: “Across The Sea”, “The Good Life”
Rivers Cuomo can’t get no lovin’—and he’s pissed! In 35 urgent minutes, the Buddy Holly look-alike spits bile at himself, his mother, and every female who’s denied him some booty. The barely-mixed tracks perfectly capture the band’s frenetic energy and Cuomo’s temper tantrums, which feature lyrics that are frequently raw and disturbing but never dishonest. On Pinkerton, Weezer turns blue balls into art.
5. Of Montreal, Hissing Fauna, Are You The Destroyer?
Standout tracks: “Gronlandic Edit”, “The Past Is A Grotesque Animal”
Love the line: “There’s the girl that made me bitter/Want to pay some other girl to just go up to her and hit her!” Don’t we all? Of Montreal is digital pop music with attention-deficit disorder, full of random musical tangents with multi-layered keyboards and a liberal use of auto-tunage. It’s also fronted by the genius Kevin Barnes, who turns his cryptic lyrics into some unbelievably catchy songs.
6. Beck, Sea Change
Standout tracks: “Guess I’m Doing Fine”, “Already Dead”
From the very first guitar strum of “The Golden Age,” Beck and producer Nigel Godrich transport us into the bleak and beautiful world of a relationship ruined. Beck the Ironic Hipster is nowhere to be found—just sincere heartache delivered in that trademark monotone of his. Word has it that he wrote all the songs in just 2 weeks after he split with his fiancé of 7 years. It’s a heartwrenching story; luckily for us, Beck finds the beauty amidst the tragedy.
7. Ryan Adams, Heartbreaker
Standout tracks: “Oh My Sweet Carolina”, “In My Time Of Need”
Ryan Adams started his solo career with this brooding, stunning breakup album that has some the best moments he’s ever put on tape. The guy’s output is ridiculous—in the year 2006 he released 3 studio albums, one of which was a double album—and while some decry this as an inability to self-edit, I just think the dude has killer work ethic. Even if his records are at times uneven, he’s one of those artists for whom I’ll buy everything he releases because his greatest songs are some of the best I’ve ever heard.