10. Kanye West – 808s & Heartbreak (2008)

We should have known better than to underestimate Kanye West. After a multi-platinum trilogy of albums, 808s & Heartbreak was West’s first album not to receive universal acclaim. The use of Auto-Tune almost guaranteed West’s jarring, alienating detour would sound dated by 2009. Instead, a strong argument can be made that 808s & Heartbreak is the Kanye West album that has aged the least since its release. Sure, West’s ever-reliable studio innovativeness is one reason the album continues to win new fans, but the overall feeling of heartache stemming from both the tragic death of his mother and the high-profile end to his engagement strike a far more universal cord than anything he’s done since.

9. Bon Iver – For Emma, Forever Ago (2008)

The warmth exuded in the intro guitar of the leadoff track “Flume” almost sounds like a salve to a wounded heart. Physically worn down by a case of mononucleosis and the end of his relationship with his girlfriend, Justin Vernon literally hibernated for three months in a cabin. What emerged was a lonely, soulful album that quickly went from indie phenomenon to instant classic.

8. Adele – 21 (2011)

Almost two decades before “Rolling in the Deep” became an all-purpose kiss-off, Liz Phair sang about turning her disgust into fame. Adele heeded that advice and with 21, she made an album that made so much money that she could retire now and live a life of luxury that most of us can only dream of. The cost, of course, was wading through a tumultuous breakup that poured out in all of 21‘s 11 tracks. When 21 reached the prestigious diamond-platinum sales mark, it marked one of the first times in 20 years that a contemporary 10 million-plus selling album could rightly be mentioned alongside such a similar commercial and artistic blockbuster like Carole King’s Tapestry.

7. Fiona Apple – When the Pawn… (1999)

In the late 1990s, lazy music journalists tried to lump Paula Cole, Meredith Brooks, Joan Osborne, and Fiona Apple into a generic “Lilith Fair” label. Apple herself received a stinging backlash thanks to a so-called controversial MTV Video Music Awards acceptance speech when she dared to say that people should follow their own individual path. All it would have taken was a typically weak sophomore slump album and Apple could be regulated to the discount bins of ’90s nostalgia. Instead, she returned with a lush, complex album that made the concept of love feel like a trauma ward.

In “Paper Bag”, Apple sings “Hunger hurts but starving works when it costs too much to love”. In “Fast As You Can”, she pleads a suitor to hit “eject” before things get ugly. She’s made two great subsequent albums rooted in heartbreak, but When the Pawn… is still the preferred accompaniment to a bottle of wine and stack of photographs of a significant other ripe for the burning.

6. Aretha Franklin – Spirit in the Dark (1970)

In the 1960s, Aretha Franklin was an unimpeachable figure of strength in both the civil rights movement and in the women’s liberation movement. “Respect” and “Think” were defining statements of strength and empowerment. But in 1970, Franklin released an album that was stripped of heroics and showed a person facing the very ordinary and very painful experience of a dissolving marriage. With tracks like “The Thrill Is Gone (From Yesterday’s Kiss)” and “Why I Sing the Blues”, Franklin provided her own personal wake to the free love moment in the 1960s. Spirit‘s dark tone initially cost the album in sales, but decades later, it’s an album is regarded as one of her best.

5. Bruce Springsteen – Tunnel of Love (1987)

Speaking of rock icons whose work almost felt superhuman, Bruce Springsteen’s Born in the U.S.A. was practically declared a modern-day national anthem in the mid-’80s, much to Springsteen’s protest (not to mention those who read the lyrics). Anything less than the bombast of another Born in the U.S.A. or Born to Run would be deemed a radical left turn <.i>a la his stark 1982 masterpiece Nebraska. Instead, Springsteen kept some of the ’80s production, left out most of the E Street Band, and released an album confronting all of the fears and doubts that come with a failing marriage, or even starting a new one.

In “Brilliant Disguise”, Springsteen plays the role of loving husband as daftly as he plays the role of rock star, with the full knowledge that both are just a role waiting for the facade to drop when no one’s looking. Even in a more hopeful setting like the new couple in “Tougher Than the Rest”, lines like “Around here baby, I learned you get what you can get” show even the honeymoon period will be littered with baggage.

4. Beck – Sea Change (2002)

It’s telling that Gen-X’s own Blood on the Tracks is an album where the predominant mood is not bitterness, but resignation. There are very few moments of genuine bile or accusatory scorn on Beck’s 2002 masterpiece (and arguably the last time he released an album that many considered was “Album of the Year” material). Instead, we get “Life goes where it does” in “Round the Bend” or the weakened response “Guess I’m Doing Fine”. The most telling moment is in “Lost Cause” when he waves the white flag, declaring “I’m tired of fighting … fighting for a lost cause”.

Even recruiting his father for the string arrangements, Sea Change is an album that sounds like someone who is using every bit of studio wizardry and musical craft to cope with the breakup of his girlfriend Leigh Limon. People who were steadfast fans of his so-called tossed off effort Mutations knew there was a soul behind the artist who gave us Midnight Vultures and “Beercan”. Sea Change more than affirmed that belief.

3. Marvin Gaye – Here, My Dear (1978)

One of the great paradoxes of modern music is that the artist whose best known material was synonymous with lovemaking released one of the grandest recordings of love’s implosion. During recording, Marvin Gaye was plagued with financial hardships due to overspending and an impending divorce from his first wife Anna Gordy. An agreement with Gordy and Gaye’s attorneys was reached and Gaye agreed to give half the proceedings of his next album to her. The result of that labor was a massive double-album that included seven-minute plus ruminations on loss and heartache. Within a year, the relationship with his second wife ended.

2. Fleetwood Mac – Rumours (1977)

The mythology behind Fleetwood Mac’s Rumours has been told so much that nothing new can really be said about an album that defined the “Me” decade of the 1970s. The only new thing that can be brought to the table is the experience of every new listener, and that listener imagining themselves being locked in a studio with the person who hurt them most for 12 hours a day for months on end. There are almost too many barbs to list on Rumours: “Shacking up is all you want to do”, “Did she make you cry, make you break down”, “Players only love you when they’re playing”. With all the turmoil, Christine McVie’s “Songbird” comes off as one of best “ceasefire” songs of all time, but it’s also segue into the most volatile track on the album, “The Chain”. More than 30 years after its release, Rumours remains the standard bearer for relationship angst.

1. Bob Dylan – Blood on the Tracks (1975)

The number four pick on this list pretty much gave this one away. Rumours may be the album that better personifies the disintegration of a relationship, but whenever an artist releases an album dealing with a breakup, people still say, “That’s their Blood on the Tracks.” Recorded while he was separated from his wife Sara, Blood on the Tracks ushered in Bob Dylan’s second wave of great material after a few underperforming (and one critically hated) albums. Blood on the Tracks had Dylan express almost the full spectrum of emotions that make up a life-changing breakup, from petty callousness (“Idiot Wind”) to plainspoken confessions (“I took too much for granted” Dylan confesses in “Shelter from the Storm”). It gave Dylan an album that could finally be compared to his early greats, but it also gave us a template for which all other breakup albums are gauged.