Sarah Silverman Picks Thirteen Songs that Will Tear Your Heart Out

In 2009, foul-mouthed comedian Sarah Silverman and goofy late-night send-up Jimmy Kimmel publicly ended their six-year relationship. Before they split, the two seemed inseparable. They were the First Couple of Comedy, famous for their rolicking game of viral video one-upmanship, which involved singing about fucking Matt Damon and Ben Affleck, respectively. They appeared in Esquire together. Silverman was a frequent fixture on Kimmel’s couch. They even reunited or a short spell. So to see two people who seemed so right for each other fail to work things out was, in a word, heartbreaking.

“I love me some heartbreak,” admits 40-year old Silverman from her home in Los Angeles. But don’t pity the best-selling author of The Bedwetter: Stories of Courage, Redemption, and Pee. These days, she’s in such high demand that a committed relationship might have to wait.
In addtion to developing a sitcom for NBC, she stars in this fall’s Take This Waltz, a tender romance directed by Sarah Polley. Silverman plays a recovering alcoholic who witnesses the cracks in the marriage of her brother (Seth Rogen) and his straying wife (Michelle Williams). In real life, Silverman avoids alcohol, relying instead on long walks through New York, “especially late at night when the streets are emptier.” That, and songs about pain. Here, we asked her to tap into that special, one-of-a-kind agony that comes from an aching heart, and choose 13 songs that might help one get through it.
Johnny Cash’s “Hurt” I believe this song is about heroin addiction. But to me, it’s about how pain means feeling something, and is therefore better than feeling nothing at all. I guess it’s why cutters cut and why some people pick fights in bars. It’s proof you exist.
She and Him’s “Sentimental Heart” This is a great breakup song by Zooey Deschanel and M. Ward. It’s the perfect soundtrack to heartbreak, and it came out at just the right time to lull me into a downward spiral. O-o-old habits die hard when you got / when you got a sentimental heart.
Rilo Kiley’s “Does He Love You?”
This was the first song I heard by Rilo Kiley and it reminded me of Janis Ian in how seriously it takes itself—in a great way. I love that it’s very melancholy, but in the end comes to fruition with a furious crescendo.
The Killers “All These Things That I’ve Done”
I love this song for many reasons, mostly because it’s anthemic. I also very much enjoy songs that have different parts—“A Day in the Life,” “Scenes From an Italian Restaurant,” “Layla.” Seeing the Killers live just enhanced that love. Brandon Flowers is so charismatic, you can’t take your eyes off him.
Janis Ian’s “In The Winter”
This is the most dramatic song there is. It’s about a woman who’s deeply alone and desperately in love with a taken man who doesn’t love her back. You have a    lovely home / just like a picture / No, I live alone / I found it easier / you must remember how I never liked / the
party life / up all night / lovely wife / you have a lovely wife.
Conor Oberst’s “Cape Canaveral”
This song was playing on the radio at a crucial time for me. The lyrics, for whatever reason, gave me the strength to change something that was wrong in my life. Victory’s sweet/even deep in the cheap seats. It brought me back to what’s important at a time when I was compromising all that because of all sorts of fears.
Janis Ian’s “At Seventeen”
Again with the Janis Ian. This whole album is heartbreaking. She wrote it when she was 17 and every song is super sad and super perfect. As you might imagine, it’s about being 17 and having no friends and no one to love and feeling awkward and alone. The first time I did stand up on Letterman (they let you pick the music you come out to), I had them play me in with “At Seventeen.” Which is not a comic’s usual choice for getting the audience pumped.
Patty Griffin’s “Long Ride Home”
This is one of my all-time favorites. It is heartbreaking. It’s about a woman who just buried her husband of many years and is now riding home in the limo from the funeral, heading towards her new life alone and reflecting on everything she did and didn’t say.
Mary Gauthier’s “I Drink”
This woman is amazing. She cuts to the core with simple words, simple storytelling, and she transcends so much pain—it’s awesome. Fish swim/Birds fly/ Daddies yell/Mamas cry/old men sit and think/I drink.
Jenny Lewis’ “Born Secular”
Jenny Lewis is the lead singer of the amazing Rilo Kiley, and she’s done some solo albums that are equally brilliant. This is a song about disillusionment and the absence of God (from what I can tell). There are not a lot of lyrics, but when the words run out the music continues for a long time, with the drums building and building in the coolest way.
Akron/Family’s “Don’t Be Afraid, You’re Already Dead”
This song was on the World’s Greatest Dad soundtrack and it touched me so deeply when I heard it. Lyrics like Don’t be afraid/It’s only love repeated over and over with additions and slight changes in the arrangements—it’s the kind of stuff you need to have pounded into your head.
Fiona Apple’s “Love Ridden”
I think this song is about a woman who has given up on a man she loves but knows isn’t right for her—maybe? Anyway, it’s beautiful and sad.
Adele’s “Someone Like You”
From the stark piano to the resignation in her voice—oh, this song. It makes you happy to be sad and alone.
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