1. “Hey Ladies” by the Beastie Boys
[youtube http://www.youtube.com/watch?v=Naf5uJYGoiU&w=600&h=375%5D
Hey ladies in the place I’m callin’ out to ya,
There never was a city kid truer and bluer,
There’s more to me than you’ll ever know,
And I’ve got more hits than Sadaharu Oh
Although this song off of Paul’s Boutique is ostensibly all about the Beastie’s sexual exploits, their self-deprecating wit and sardonic style reveal it to be little more than good-natured bluster. There’s something about the way these three effortlessly combine on verses, finishing each other’s lines and rapping in tandem, that gives you the distinct idea that they spent a lot more time with each other than with any ladies. The result is that instead of feeling like you’re listening to douchey guys share their conquests, you feel like you’re hearing three high school freshmen tell tall tales and drop innocuous in-jokes. “Hey Ladies” is endearing and fun, and a great tune to enjoy while pouring out some of your 40 for MCA.
2. “Longview” by Green Day
[youtube http://www.youtube.com/watch?v=42BBdzzgPNM&w=600&h=375%5D
When masturbation’s lost its fun,
You’re f-cking lonely
This song is about being a loser who stays at home watching TV and masturbating all day, a topic which I can assure you this writer knows nothing about. Nope, not Ted Pillow – I’m the kind of guy who spends upwards of an hour out of the house each day and rarely masturbates.
Moving on, “Longview” is also about the dangers of becoming a couch potato; it perfectly captures those feelings of despair and self-hatred that fester when you lie around eating Doritos, watching people far more attractive than you have romantic relations with each other on TV.
3. “Why Bother?” by Weezer
[youtube http://www.youtube.com/watch?v=C11KeB7O2vk&w=600&h=375%5D
I know I should get next to you,
You got a look that makes me think you’re cool,
But it’s just sexual attraction,
Not something real so I’d rather keep whackin’
You’ll notice that both “Longview” and “Why Bother?” are part of a long tradition of songs about masturbating. For obvious reasons, the DNA of this particular genre is intricately intertwined with that of the “Not Getting Laid” genre. More specifically, “Why Bother?” is a “the glass is half-empty” take on relationships — why bother getting involved in them when you can just masturbate? One man’s take: either way, you’ve certainly got your hands full.
4. “867-5309/Jenny” by Tommy Tutone
[youtube http://www.youtube.com/watch?v=axLRUszuu9I&w=600&h=375%5D
Jenny, Jenny, you’re the girl for me,
Oh you don’t know me, but you make me so happy
One of everybody’s favorite 80s pop songs is, rather bizarrely, about a guy falling in love with a girl whose name he finds written in a bathroom stall. This is clearly the behavior of a man who: 1.) Makes awful, awful decisions, 2.) Hasn’t had sex in quite a while, and 3.) Isn’t sure exactly how to go about wooing the opposite sex. Unfortunately, focusing all of your hopes and yearnings onto a phone number carved over a broken toilet paper dispenser is neither wise nor hygienic. On the other hand, this guy would love the “personals” section on Craigslist.
5. “I Wish” by Skee-Lo
[youtube http://www.youtube.com/watch?v=Zyf0YwUJcqk&w=600&h=375%5D
And do you really wanna know what’s really whack,
See I can’t even get a date,
So, what do you think of that?
I heard that prom night is a bomb night,
With the hood rats you can hold tight
I’m not really sure what happened to Skee-Lo after this song, but the only safe assumption is that a territorial Cee Lo, angered by the name similarity, ate him. Regardless, “I Wish”, released at a time when rap was entering a particularly violent and misogynistic period, brought some much-needed levity and humor to the game. It showed that driving a crappy car and getting no love from girls is okay, as long as you can be honest and laugh at yourself about it.
6. “I Will Possess Your Heart” by Deathcab for Cutie
[youtube http://www.youtube.com/watch?v=pq-yP7mb8UE&w=600&h=375%5D
You reject my advances and desperate pleas,
I won’t let you, let me down so easily, so easily
This eight-minute ode to creepiness recently surpassed The Police’s “Every Breath You Take” on my list of favorite songs to stalk to. It is hypnotic enough to disguise the unnerving subject matter, and mesmerizing enough to make you forget that even the title is way too much information. Make sure you put this on your iPod before grabbing your binoculars and looking for a comfortable tree outside the bedroom window of your unrequited love.
7. “I Want you to Want Me” by Cheap Trick
[youtube http://www.youtube.com/watch?v=HBQ9dm7zaQU&w=600&h=375%5D
I want you to want me,
I need you to need me,
I’d love you to love me,
I’m begging you to beg me
“Oh god, alright already, I’ll sleep with you! Christ, you’re pathetic. And for the last time, NO, you did not see me crying!”
8. “Creep” by Radiohead
[youtube http://www.youtube.com/watch?v=XFkzRNyygfk&w=600&h=375%5D
But I’m a creep,
I’m a weirdo,
What the hell I’m doing here?
I don’t belong here
I wouldn’t recommend using the above lyrics as personal affirmations, but I do occasionally find them entering my head during social gatherings. I usually combat the overwhelming sense of not-belonging by quietly excusing myself from the room, walking to a place where I can be alone for a while, and slamming my head repeatedly against a hard surface until I regain some sense of composure. Either way, I certainly have never associated this song with getting laid, I can tell you that much.
9. “Passin’ Me By” by The Pharcyde
[youtube http://www.youtube.com/watch?v=QjsPG0Kspxo&w=600&h=375%5D
Now there she -goes again, the dopest Ethiopian,
And now the world around me be gets movin’ in slow motion,
Whenever she happens to walk by – why does the apple of my eye,
overlook and disregard my feelings no matter how much I try?
“Passin’ Me By,” The Pharcyde’s biggest hit, deals with the bittersweet memories of childhood crushes that never came to fruition. Rapping with equal parts honesty and regret, the group delivered one of the most critically respected hip hop singles of the 90s. Plus they are all upside-down in the video, which is totally awesome.
10. “In My Room” by The Beach Boys
[youtube http://www.youtube.com/watch?v=1fQT-GjKlLw&w=600&h=375%5D
There’s a world where,
I can go and,
Tell my secrets to,
In my room,
In my room
Singing about your room as a refuge from the world — a place where you are free to cry and share secrets — is an emphatically effective way of revealing yourself to be a nerdy virgin; let’s just say that the bedroom in question didn’t sound like it had a lot of guests. The Beach Boys can sing whatever they want and still be fighting off bikini-clad surfer chicks, but I wouldn’t recommend this for anyone else; probably best to keep these thoughts in your diary.
11. “The Saturday Boy” by Billy Bragg
[youtube http://www.youtube.com/watch?v=b6Pla-HfGAs&w=600&h=375%5D
In the end, it took me a dictionary,
To find out the meaning of unrequited,
While she was giving herself for free,
At a party to which I was never invited
Sparse and kind of beautiful, “The Saturday Boy” is another song about adolescent infatuation, perhaps the most powerless and despairing of all the sexless scenarios listed above. Plus the lyrics are amazing.
12. “On a Rope” by Rocket from the Crypt
[youtube http://www.youtube.com/watch?v=777kGx7-qLw&w=600&h=375%5D
No gun, no bomb, no way I’ll run,
Too bad, I’m not in shape,
Too little, too late, that deal’s so chaste,
Do burning hands seem to care?
The narrator of Rocket from the Crypt’s “On a Rope” beseeches a “chaste” would-be lover who has him “On a rope, on a rope, got me hanging from a rope.” Bouncy rhythms and catchy sing-a-long chorus aside, I think we can all agree that this particular rope sounds maddeningly PG-rated. In fact, by the end of the song, he’s not too proud to fall to his knees and start begging — a tactic that I have found to elicit little besides pity.
13. “Chemistry” by Jawbreaker
[youtube http://www.youtube.com/watch?v=NNWnjSe5Iiw&w=600&h=375%5D
This school’s a living hell,
I work and don’t get paid,
I smoke a lot but can’t get laid
Jawbreaker’s “Chemistry” details several of the miseries of high school, including the inability of the song’s narrator to (presumably) lose his virginity. Said narrator pines that it’s “seven months to June (and even then, so what?)” and idly dreams of a girl two years younger. Unfortunately, “some older guy with a motorbike picks her up after school.” Well, there’s always college, bud! Also, it might help if you stopped using words like “motorbike.”
14. “Just a Friend” by Biz Markie
[youtube http://www.youtube.com/watch?v=9aofoBrFNdg&w=600&h=375%5D
So I came to her room and opened the door,
Oh, snap! Guess what I saw?
A fella tongue-kissin’ my girl in the mouth,
I was so in shock my heart went down south
One of a kind rapper/crooner Biz Markie delivered the ultimate cautionary tale of getting strung along with this hit that garnered him his only mainstream success. Despite repeated attempts on the part of Biz to establish that his potential mate was single, he discovers by the song’s end that she’s been hooking up with the guy she had claimed was “just a friend.” Markie’s slow-motion flow, nursery rhyme delivery, and distinctly unpolished voice make this one perfect for bitter, drunken karaoke. 
