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.

It wasn’t my first peck on the lips (that was during a John Patrick Shanley scene for drama class). Nor was it the first Spin The Bottle make-out session (thank you Hebrew School!). This was the first kiss. You know the one I’m talking about—where time stands still, the earth stops spinning on its axis and the angels in your head cry out, “Hallelujah!” even though you have no idea what you’re doing and you inevitably use way too much tongue.

It was the summer before sophomore year, on a campground somewhere in Utah. She was a Jersey girl, but to protect the innocent, let’s keep names out of it.

We found each other on a charter bus in the southwest United States. It was me, her, Scott, and about 40 other teens whose parents had signed them up for this traveling summer camp called a Teen Tour. We stayed at college dorms and campsites on the way to some of the biggest tourist attractions in California, Utah, Arizona, and Nevada. Scott and I flew out to meet the group in San Francisco, the starting point of our three-week journey.

I noticed her immediately. She was fair-skinned with dark brown hair, the kind of girl whose pale cheeks turned pink when the wind blew cold. I remember she looked best right when she woke up. One morning, I watched her come out of her tent at our campsite in Lake Tahoe. She was draped in sweaters, her arms folded across her chest as she shivered from the chill. It was the first time I was overcome with this urge to want to kiss somebody…and it was immediately replaced with the horrifying realization that I’ll never have a chance with this girl.

You see, up until that point, some of the more influential gossipers in junior high had branded me as a dork. And I couldn’t really argue; the evidence against me was stacked too high. I was the piano-playing, Broadway-singing, boisterous prepubescent nerd whose round features begot an athletic disability unseen by anyone else on the basketball court. During little league scrimmages, I silently prayed to get picked on the team that wore shirts—not skins—because let’s face it: no one wants to pass the ball to the slow kid with glasses and bitch tits.

It was a predicament. I had zero confidence around girls, yet I badly wanted to profess my love to the prettiest, most popular girl on this summer excursion. Luckily, this Teen Tour provided a unique opportunity. Sure, back in junior high bullies would routinely shout “Hey pianist!” (as in, “Hey, PENIS-t!”) as I walked down the halls. But here, nobody knew who I was. I could leave my dork ways behind and become someone new, someone bold, someone cool.

It took the entire three weeks to build up the nerve to tell her how I felt. Finally, three days before the trip was over, I found myself standing next to her while waiting in line for ice cream at the Bryce Canyon Visitor’s Center. No one else was around, and I knew it was my only chance. So I took a deep breath, and with the most romantic Shakespearean prose I could muster, I tapped her on the shoulder and uttered:

“I uh…really like you.”

Three terrible, interminable seconds of silence.

Then: “Um, David, I have to go to the bathroom.”

Ok, so it didn’t go exactly as I planned. But rather than pester her (or worse, follow her into the bathroom), I kept my distance, put a smile on my face, sat a few rows back from her on the bus and pretended that I wasn’t fazed. Later that night, as we were sitting around the campfire, she leaned over and asked me if I wanted to go for a walk. We left the group and strolled over to the tents by the lake. As we walked towards the water, I could hear the distant crackle of roasting marshmallows over the constant chatter of my own teeth either from the nerves, the cold, or both.

I apologized for putting her on the spot earlier that day. She said it was okay. She said she actually kind of liked me too. I felt this surge of confidence sweep through me, so I turned to her and said, “I really want to kiss you right now.” And right there, by the lake, under the stars and the shining moonlight, I had my first kiss.

Things were never the same after that summer. I grew a couple of inches, got contacts instead of glasses, cut my hair, and stopped wearing criminally short shorts. I walked a bit taller, smiled a little broader. By the time I was a sophomore, getting the big part in the spring musical and playing the hell out of a classical tune wasn’t so uncool anymore. But most importantly, I didn’t care what anyone else thought about me. I never felt like a dork again, because I had my first kiss.

1. Ryan Adams, Easy Tiger

Standout tracks: “Two”, “Everybody Knows”

My roommate’s girlfriend can’t stand Ryan Adams, but she always adds a touch of class when she sings her version of the chorus at the top of her lungs: “It takes two when it used to take duuuuuumps!”

2. Air, Talkie Walkie

Standout tracks: “Run”, “Universal Traveler”

One of the great stoner albums of our time. Producer Nigel Godrich is a master at creating soundscapes so vivid you can almost reach out and touch them (see Beck’s Sea Change, every Radiohead album).

3. Badly Drawn Boy, About A Boy, Original Soundtrack

Standout tracks: “Something To Talk About”, “Silent Sigh”

A gloriously fun listen, this is one of my all-time favorite pop records. Great movie, too. And while we’re on the subject, Nick Hornby’s one of my favorite writers, even though I can’t stand top 10 lists.

4. A Funny Thing Happened On The Way To The Forum, 1996 Broadway Cast

Standout tracks: “Everybody Ought To Have A Maid”, “Comedy Tonight”

I saw a tiny community theatre production of this in South Florida and immediately fell in love with the material. I had to go back to see it again during its two-week run, and even though I was one of 4 people in the audience, I was laughing my ass off. One of Sondheim’s liveliest scores, this recording features Nathan Lane hamming it up in the starring role.

5. David Gray, Life In Slow Motion

Standout tracks: “The One I Love”, “Slow Motion”

In my dreams I get to work with producer Marius de Vries, mastermind behind the beautiful orchestral arrangements heard here and on albums like Rufus Wainwright’s Want One and Björk’s Debut.

6. The Hives, The Black And White Album

Standout tracks: “Try It Again”, “Won’t Be Long”

I saw these guys open for Maroon 5 without knowing a song, and by the time they finished their half hour set, I was a believer. Their cocky/funny shtick is a riot, and their hard rock rips off Iggy Pop in the best way. I’ve always wondered how guys like Howlin’ Pelle Almqvist can scream all night long and still sing the next day.

7. Billy Joel, River of Dreams

Standout tracks: “A Minor Variation”, “Two Thousand Years”

Here your favorite neighborhood Piano Man gets pissed off about his manager fucking him out of 90 million dollars and churns out his most up-tempo tracks to date. The B-sides from this album are my most coveted surprise setlisters at his concerts.

8. Elliott Smith, XO

Standout tracks: “Tomorrow Tomorrow”, “Bottle Up And Explode!”

I suffered from a hardcore sophomore slump my second year at Stanford, and for about 3 months Elliott Smith was the only artist that seemed appropriate to listen to. Depressing as hell, but nothing else sounds so beautiful when you feel like shit.

9. Talking Heads, Stop Making Sense

Standout tracks: “What A Day That Was”, “This Must Be The Place (Naïve Melody)”

Jonathan Demme’s groundbreaking concert film—best ever made?—showcases the manic stage antics of David Byrne, one of rock’s original weirdos. On early studio albums we get Talking Heads the experimental art-school punks, but here we get Talking Heads the rousing funk party band. A big thank you to my roommate Kenton for bringing out my inner Psycho Killer.

10. Ben Folds Five, Self-Titled

Standout tracks: “Philosophy”, “Underground”

Most people know Ben Folds Five from the radio hit “Brick” off their second album, but I prefer the attitude and gleeful pop sensibilities of their first record. Totally original and smarmy as hell.

Billy Joel’s Greatest Hits proved such a tremendous listen that I went and bought every album by the guy.

The exciting thing about discovering a prolific artist who is done making music is that you can buy it all at once. It’s like watching Six Feet Under on DVD. There aren’t any long interruptions between additions to the story—it’s all out there before you. Listening to a new band like Franz Ferdinand, on the other hand, is kind of like watching Lost: it’s fun anticipating the next installment, but I really wish I could go in a time machine and just buy the whole thing.

Looking back on it now, I can see that Billy Joel was a great introduction to pop music. His influences are so clear and disparate. When I first heard R.E.M.’s “End of the World (As We Know It)”, I thought it sounded like a ripoff of “We Didn’t Start The Fire”—little did I know it was the other way around. When I later I realized that Ray Charles’ “Georgia On My Mind” was a near carbon copy of “New York State of Mind,” I started to see how I could use Billy Joel’s music as a conduit to explore other artists. I met The Beatles through “Laura,” found Elvis in “Still Rock n’ Roll To Me,” and discovered Broadway during “Scenes From An Italian Restaurant.” When you listen Joel’s songs, you’re really just listening to his takes on different styles of music. His discography exposed me to so many parts of the Rock n’ Roll canon, and introduced me to a many great artists who made music before I was born.

The only problem was I was ten when this process started, and none of this could I talk about with my friends. Coming to school excited to discuss a 20-year old hit like “Pinball Wizard” doesn’t exactly win you cool points during recess. I found I could only share this budding, newfound interest of rock n’ roll with adults 4 times my age, so it goes without saying that after a while, I became a big hit with my friends’ moms. I never had any trouble sleeping at a friend’s house; while my buddy hooked up the Nintendo, I could always chat it up with his mother.

“Did you know, Mrs. Savitz, that ‘Only The Good Die Young’ was originally a reggae tune? Amazing, isn’t it? Now how bout those milk and cookies…”

A couple years later, I tried to use this power to get moms at temple to urge their daughters to date me.

“You should go out with that nice blonde Jewish boy,” they would say. “He knows The Jazz Singer!”

Too bad the best way to make a girl never date you is to get her mother to like you.

I know I have music inside of me. I just have no idea where it came from.

My parents never listen to music. My mom enjoys a little talk radio now and then, but my dad is the real mystery. He spends two hours in the car every day driving to and from work in silence. No talk shows, no radio, nothing. I guess the man’s got a lot on his mind.

When I started asking for piano lessons at age 8, he started to realize that music was more than just a passing interest for me. One day on the way to school, my dad asked me if I wanted to hear the kind of music he liked. I was intrigued, to say the least. I mean this was the guy I never saw once turn the radio on. When I finally got the balls to start flipping through stations in his car, I had to actually turn the air condition down just to hear what song it was. So with his son’s piqued interest and a smile on his face, my dad opened the little tray in his armrest and handed me a short stack of cassettes. His entire music collection was as follows:

1. Barry Manilow, Greatest Hits Volumes 1, 2, and 3
2. Barbara Streisand, Back To Broadway
3. The Secret Garden, Original Broadway Score; and
4. Jesus Christ Superstar, Original Motion Picture Soundtrack.

That’s it. No Stones, no Zeppelin, not even a Beatles record. My dad lived through every major milestone in rock history—Elvis’ shimmy, The Beatles on Ed Sullivan, Hendrix at Woodstock, Dylan Goes Electric—and here he was with nothing to show for it. I would’ve killed to see any number of artists from the 60s and 70s play live, and he couldn’t even remember if they rolled through town. Sit my dad in front of any jukebox, and I swear he wouldn’t know “Stairway to Heaven” from “Like A Rolling Stone.”

Thing is, my dad, like my brothers, was a jock. He kicked ass on his high school football team, and fought a few bullies when he was a kid. He even became an avid canoeist when he got older, so much so that he signed up for the 1980 Summer Olympic trials in Moscow, until the U.S. boycotted them and he never got the chance to compete.

My brothers Ivan and Adam shared my dad’s fondness for sports and even eclipsed his talent. Ivan picked up a tennis racket when he was 8, and within a few tournaments it became clear he was a prodigy. Fast forward 10 years later and Ivan is #1 in the world on the Junior tennis circuit with Adam not far behind—he became #2 in the nation at age 16 right behind Ivan.

So where does this leave me? Uh, not so good at tennis. Ever been in a fight? Nope. How’s your canoeing skills? Nada. I’ll tell you what though, my CD collection kicks ass.

Billy Joel
Greatest Hits Volumes 1 & 2

I was 8 years old when my mom took me to the grocery store and the song “Piano Man” came on the radio. At first I thought the voice sounded like a girl’s, it was so high. I can’t remember if she said it was Billy Joel, but when I think back on it now I can probably guesstimate that she had no idea who it was. You see, my mother never listens to music. Not only does she never listen to music, but the last time I came home to Florida to visit family and she picked me up from the airport, she actually had FOX News Radio on in the car. FOX News! Ugh, it hurts the heart…

Anyways, I found out some way or another that it was Billy Joel. I didn’t find it out on the Internet because we didn’t have computers back then. Shit, how did people figure things out 15 years ago? Did I go to the library and look up “old man making love to tonic and gin” in the Dewey Decimal System? Whatever, whatever my 8 year old self was a very resourceful young man, and he found out that Billy Joel’s voice was once very high, and he was, in fact, the Piano Man.

So I went to my local Spec’s and spent a whopping $30 on the double-disc album. And I fucking loved it. I didn’t know a thing about music, the piano, rock bands, nothing. I just knew that when I played this record, it made me happy.

My folks had a baby grand piano in the living room and I sat down on the tall piano bench and tried to figure the songs out. Finally, one day I asked my mom for piano lessons.

My mom told me she tried giving piano lessons to my brothers, and they hated it. She was sparing me from something I wouldn’t like, she said. But I pressed on, and my mother found this nice Jewish lady who advertised in my elementary school yearbook so I got a piano teacher.

This album was my introduction to the piano. My introduction to music itself, really.