“Remind me,” Mike Doughty asked. “What are we trying to do again?”

I wasn’t so sure anymore. When I started exchanging emails with Doughty — the singer-songwriter you might remember from such albums as Skittish and Haughty Melodic, or as the former frontman for Soul Coughing — I had ambitious schemes. It was, at least in my head, a bold experiment in post-modern music appreciation, where the lines between artist and fan would become blurred and an activity once passive was now intensely interactive. Doughty and I were going to create if not the greatest mix-tape of all time, at least the most innovative and unprecedented. It would be like that scene in Back to School where Rodney Dangerfield hires Kurt Vonnegut to ghostwrite an essay about Vonnegut’s novels, or the scene in Annie Hall when Woody Allen pulls Marshall McLuhan from behind a movie poster to humiliate an academic boob. Allen quipped at the time, “If life were only like this.” Well, in 2011, it actually can be. McLuhan and Vonnegut are both dead now, but if they weren’t, it’s quite possible they’d have their own Twitter and/or Facebook accounts. Social media has made everybody more accessible. You can’t pull an author or philosopher out of thin air to do your bidding, but you can certainly Tweet him and ask.

Which is what happened with Doughty. We’re Facebook friends and mutual Twitter followers. I learned that he has a few upcoming projects — a new album called Yes and Also Yes, and a memoir called The Book of Drugs, both coming out at some as-yet-unspecified date in the nearish future — so I made him an offer. I’ll plug your stuff if you curate an essential mix-tape of your own songs. He said yes, and it became “The Most Important Thing I’d Ever Do In My Life.” What any of it signified, I couldn’t tell you. But I could feel it in my bones that this was a big deal, some kind of meta-meta statement on social media and music and technology, which are all things that “Are Important” and any self-respecting journalist worth his salt should be writing about.

But of course, as with all grandiose plots, it wasn’t nearly as satisfying in execution as it was in my head. When I cooked up the idea, I imagined myself the Lester Bangs to Doughty’s Lou Reed, arguing loudly and way too passionately about the cultural significance of our favorite songs in his oeuvre. Instead, it was all very civil and unprovocative. I suggested some songs, and he mostly agreed with my choices. He asked that we not include so many Magnetic Fields covers, “so people don’t find out the sycophant I really am.” I learned that his two songs with “nectarine” in the title aren’t thematically connected, so we agreed, with a depressing lack of contention, that we didn’t need to include them both. I asked if “Frog and Banjo” was too obvious an attempt to flaunt my knowledge of his musical obscurities, and then Doughty asked for the mp3 (”I lost mine somewhere”), so I never really got an answer. After almost no debate, we agreed on 10 to 12 songs that anybody who likes Mike Doughty would agree: “Yep, those are all pretty good Mike Doughty songs.”

“Am I supposed to be (fake) arguing about whether these songs should be on the purported mix-tape?” Doughty asked in an email. I didn’t know what to tell him. Asking for permission to argue, even (fake) argue, kinda takes all the fun out of arguing. And even if he was willing to engage me in a spirited musical polemic, what was the fucking point? What exactly was I proving other than that Mike Doughty would return my emails? It was less like pulling Marshall McLuhan from off-screen to make a mockery of intellectual hubris and more like the old “Chris Farley Show” sketch from Saturday Night Live. “Remember that song ‘Rising Sign’ from Skittish, where you’re like ‘I’d drink the fuel straight from your lighter’? That was awesome.”

The last time I made a mix-tape in earnest was 1996. It was for my then girlfriend and future wife, prior to our first-ever date at a Soul Coughing show (Mike Doughty’s former band) at Chicago’s Metro theater. Because I hoped our date would lead to sex — a carnal “Bus To Beelzebub,” if you will — I tried to impress her with my knowledge of Brooklyn hipster musicology by making her a Soul Coughing mix-tape prior to the concert. This was entirely unnecessary, as the band had only released two albums, Irresistible Bliss and Ruby Vroom. But it was never about a musical retrospective or indie-rock primer as much as romantic DJing. A mix-tape, at its best, is an attempt to have an intimate conversation with somebody by putting songs in a different order. Every song sequence was teeming with significance. It meant something that the mix-tape began with “True Dreams of Wichita,” my least favorite Soul Coughing song which just so happened to be her favorite. When Doughty sang about wanting to “grip her love like a driver’s license,” he might as well have been a direct message to my girlfriend, although I don’t know what that message might’ve been, other than that it sounded vaguely dirty. (Was “her love” a vagina? God, I hoped so.) Every song had significance, from the arty romanticism of “Lazybones” and “Janine” to the nerdy sensuality of “So Far I Have Not Found the Science” and “4 Out of 5.”

The mix-tape did the job. Obviously, because she married me. And I haven’t made a mix-tape since. Partly because it’s never a good idea to make a mix-tape for somebody you’re not fucking or trying to fuck, because a mix-tape is nature’s way of saying “I totally want to fuck you. Please allow these songs to explain why.” Also, there is no such thing as “mix-tapes” anymore. If you say to somebody “I would like to make a mix-tape for you,” their first reaction (if they’re older than 30) will likely be “You’re married. Stop trying to fuck me.” And if they’re under 30, they’ll look you right in the eyes and ask, “What in the goddamn hell is a mix-tape, old man?” And then you can either explain what a cassette tape is or slink towards the nearest exit, the latter of which is probably a better idea, because she’s right, you’re way too married to be flirting with her that hard, and she’s far too young to give a shit about “Super Bon Bon.”

I miss mix-tapes. Not just the antiquated technology, but what they represented. Giving somebody a mix-tape was a bold gesture, akin to brushing a hand across the breast of a stranger in a crowded bar. It was sexual bravado for the timid, a smattering of sexually suggestive songs that harmonized on your behalf: “Yeah, that just happened. You wanna make something of it?” Mix-Tapes have been replaced by playlists, which don’t really allow for as much one-on-one interaction. You don’t give somebody a playlist. You make one on your iPod, and then you enjoy it in isolation. Music has become more about navel-gazing and less about forcing your musical tastes on people you find physically attractive. Which is kind of tragic, because at its core, music, at least the music that actually matters, is about expressing your romantic intentions to people you find physically attractive. Making a playlist for yourself kinda defeats the purpose, unless you’re trying to seduce yourself, in which case… good luck with that. But pairing The National’s “Slow Show” with Broken Social Scene’s “Anthems For A Seventeen-Year-Old Girl” is not going to make masturbation any sweeter. Trust me, I’ve tried.

Thinking about those old mix-tapes, it suddenly made sense why I’d been running into the same dead end with the Great Mike Doughty Mix-Tape Experiment. We were assembling songs using a vague “best of” criteria, and that has no soul, no emotion, no erotic end-game. We had forgotten the raison d’être of a good mix-tape. It’s really no different than why Woody Allen pulled Marshall McLuhan from behind a movie poster in Annie Hall. It wasn’t an accident that he did it while Diane Keaton, his on-screen and off-screen lover, was standing right next to him. Because in the end, why bother being clever if there’s no chance it could lead to getting laid?

I emailed Doughty and explained everything; I told him about the Soul Coughing show in Chicago with my future wife, and the Soul Coughing mix-tape that preceded it, and how that mix of his songs resulted in my seeing her naked, and then seeing her naked countless times since. But that was fifteen years ago, and I needed a fresh musical aphrodisiac. I asked him to construct a mix-tape of his songs that possessed what may be the most vital ingredient in any music collection: sexual tension.

He understood immediately. There were no more emails of “What do you want exactly?” We were speaking the same language. In a matter of hours, he concocted the following mix-tape blueprint, including detailed explanations on exactly how and why these particular songs will result in coitus. “If you play them all,” Doughty wrote, “in this exact order, it will make the person you give it to want to have sex with you. I guarantee it. You have my word as a gentleman.”

He’s not kidding. I say that from experience.

*    *    *

Mike Doughty’s Mix-Tape Guaranteed to Get You Laid


This song’s about going to school with 26 women named Jennifer who are horrible, and one Jennifer who’s amazing, and they all hate her for her beauty and kindness. Because you can tell any woman named Jennifer that it’s about her — and Jennifers aren’t hard to find, are they? — you’ll definitely get some.


This is a song about what a friend of mine calls an “Ass Fast” — to purposely avoid sex for a while. So the tone of the song is, like, look at those beautiful women, I’m not gonna do it with them. This will get you some because the person in question will be flattered that you dig her enough to end the ass fast.


Also about an ass fast, but with actual attempts to talk the person — who worked the counter at Tiny’s Giant Sandwich Shop circa 2003 — out of it: “I’m not worth your time, I’ll drag you down.” Extreme self-deprecation is muy sexy, so you’ll get some.


Guy’s playing a show to a near-empty club, except for a lone beautiful dancer. He keeps playing only so she keeps dancing. There’s this lyric: “I love your baby fat, your crooked nose is where it’s at.” Women love having their flaws pointed our, so you’ll get some.


This is a song about a girl I was in love with in school who dropped me like a hot rock. I had this vindictive fantasy when she ditched me, that I’d write a big hit song sneering at her, and she’d be at her job waitressing at Bandito’s on MacDougal Street, and she’d feel bad. Women enjoy songs about the misfortune of waitresses, so you’ll get some.


About an ex so thoroughly shitty that I ask her if she’s purposely being wretched so she’ll get dumped. In the second verse, I say she’s so horrible that she makes me feel like I’ve sniffed way too much cocaine and I’m bugging out. PS, in real life, after I wrote the tune, I did not give her the boot, but discovered months later that SHE REALLY WAS TRYING TO BE SO AWFUL SHE’D GET DUMPED. So, if you just comply and dump her, you can go out and find a less terrible girlfriend, and you’ll get some.


I had a girlfriend with this gorgeous name that I was unable to use as a song title. There was something tricky about it. Since you can tell anyone with any name that it’s about her, you’ll get some.


About a woman so wasted all the time that you’d feel bad macking on her. Will get you some because she can be confident you wouldn’t slip her a roofie.


Third verse is about a woman prone to freak-outs so random, it’s like a tiny monster has moved into her brain, hot-wired it, and seized control. You’ll get some because multiple-personality disorder is hot.


For one thing, the song’s about how amazing fleshiness on a woman can be. For another, the song is mostly stuff I wrote down on a piece of paper that I handed to a girlfriend and made her say into a microphone. I cut it up and mixed it into the song. Because women dig it when you dig their non-skinny-ness, and they really enjoy reading random, weirdly poetic things into a mic, you’ll get some.


Contains the lyric “Slutty fat girls in wedges; John Paul Jones, bustle in the hedges.” Both “fat” and “slutty” are meant sincerely as compliments. People in a wholehearted slutty phase are powerful and sexy and great and confident; fat just means sexy fleshiness. It mentions wedges because all woman on the planet should be deeply thanked for wearing high heels. I suggest finding a woman with amazing taste in footwear who’s into Led Zeppelin. If you sing this to her, you will get some.


This song contains the lyric “I’m seeking girls in sales and marketing/ Let’s go make out up in the balcony.” It sounds kind of like a help-wanted Craigslist ad, and women really dig job interviews. Also, sex in public places, such as movie theaters. Find an unemployed woman and you’ll get some.


Contains the line “It’s your misfortune that sweetens my song.” Women like it when dudes are turned on by bad luck, so you’ll get some.

(This story originally appeared, in a slightly different form, in MTVHive.com.)