D.V. DeVincentis, Steve Pink, John Cusack and Scott Rosenberg - High Fidelity - Five Most Painful Breakups lyrics

[Rob Gordon] My desert island all-time top five most memorable breakups, in chronological order are as follows: Alison Ashmore, Penny Hardwick, Jackie Alden, Charlie Nicholson, and Sarah Kendrew. Those were the ones that really hurt. (shouting so that Laura out on the street could hear him) Can you see your name on that list, Laura? Maybe you'd sneak into the top ten. But there's just no room for you in the top five. Sorry! Those places are reserved for the kind of humiliation and heartbreak you're just not capable of delivering. (he opened his window and shouted at Laura getting into her car) If you really wanted to mess me up, you should have got to me earlier! Which brings us to number one on the top five all-time breakup list: Alison Ashmore (Shannon Stillo). One moment they weren't there, not in any form that interested us, anyway. And then the next, you couldn't miss them. They were everywhere. And they'd grown breasts. And we wanted - actually we didn't even know what we wanted. But it was something interesting, disturbing even. My relationship with Alison Ashmore lasted for six hours: the two hours after school before the 'The Rockford Files' for three days in a row. But on the fourth afternoon, Kevin Bannister....It would be nice to think that since I was 14, times have changed. Relationships have become more sophisticated. Females less cruel. Skins thicker. Instincts more developed. But there seems to be an element of that afternoon in everything that's happened to me since. All my romantic stories are a scrambled version of that first one. Number two on the top five all-time breakup list was Penny Hardwick (Joelle Carter). Penny was great lookin', and her top five recording artists were Carly Simon, Carole King, James Taylor, Cat Stevens, and Elton John...She was nice. Nice manners, nice grades, nice looking. She was so nice, in fact, that she wouldn't let me put my hand underneath or even on top of her bra. Attack and defense. Invasion and repulsion. It was as if breasts were little pieces of property that had been unlawfully annexed by the opposite s**. They were rightfully ours and we wanted them back. Sometimes I got so bored of trying to touch her breast that I would try to touch her between her legs. It was like trying to borrow a dollar, getting turned down, and asking for 50 grand instead. I wasn't interested in Penny's nice qualities, just breasts. And therefore, she was no good to me...I started dating a girl who everyone said would give it up and who didn't. And Penny went with this a**hole named Chris Thompson who told me that he had s** with her after something like three dates. Number three in the top five all-time breakup list? Charlie Nicholson (Catherine Zeta-Jones). Soph*more year of college. As soon as I saw her, I realized she was the kind of girl I'd wanted to meet ever since I was old enough to want to meet girls. I mean, she was different. She was dramatic and she was exotic. And she talked a lot and when she talked she said remarkably interesting things about music, books, film and politics. And she talked a lot. And she liked me. She liked me. She liked me. At least I think she did...We went out for two years and I never got comfortable. Why would a girl, no, a woman, like Charlie go out with me? I felt like a fraud. I felt like one of those people who suddenly shave their heads and said they'd always been punks. I was sure I'd be discovered at any second. And I worried about my abilities as a lover. And I was intimidated by other men in her design department and became convinced she was gonna leave me for one of them. Then she left me for one of them. The dreaded Marco... (One rainy night, he caught Marco with Charlie) ... (A while later, after reconciling with her, he realized that she wasn't for him) And I lost it. Kinda lost it all. Faith, dignity, about fifteen pounds. When I came to a few months later, I found to my surprise I had flunked out of school. Started working at a record shop. Some people never got over 'Nam or the night their band opened for Nirvana. I guess I never really got over Charlie. But the thing I learned from the whole Charlie debacle - you gotta punch your weight. You see, Charlie, she's out of my cla**. She's too pretty. Too smart. Too witty. Too much. I mean, what am I? I'm a middleweight. Hey, I'm not the smartest guy in the world, but I'm certainly not the dumbest. I mean, I've read books like 'Unbearable Lightness of Being' and 'Love in the Time of Cholera.' And I think I've understood them. They're about girls, right? Just kidding... Anyway, me and Charlie, we didn't match. Marco and Charlie matched. But me and Sarah (Lili Taylor), number four on the all-time list, we matched. She'd just been dumped by some a**hole named Michael...I'd just been run over by Charlie...It made sense to pool our collective loathing for the opposite s** and while we were at it, we get to share a bed with somebody at the same time. We were frightened of being left alone for the rest of our lives. Only people of a certain disposition are frightened of being left alone for the rest of their lives at 26. We were of that disposition. So when she told me -- ("I met someone else")...it was contrary to the whole spirit of our arrangement. So how come I got dumped?... For a couple of years, I was DJ at a club. I was good at it, I think. And while I was doing it, it was the happiest I've ever been. And that's where I met Laura. She was already a lawyer but she worked for legal aid, hence the leather jacket and clubbing. Oh, I liked her right away...To be honest, I hadn't met anyone as promising as Laura since I started deejaying, and meeting promising women is kind of what the deejaying thing is supposed to be about. And anyway, we, we moved on from there. She lost her lease on her apartment in Lakeview, and she moved in with me. And it stayed that way for years. She didn't make me miserable, or anxious, or ill-at-ease. And you know, it sounds boring, but it wasn't. It wasn't spectacular, either. It was just - good. But really good. So, how come I'm suddenly an a**hole?...One: That I slept with someone else...while she, Laura, was pregnant...Two: That my affair directly contributed... Three: That after the abortion, I borrowed a large sum of money from her... And have not, as of yet, repaid any of it....Four: That shortly before she left me, I told her that I was kind of unhappy in the relationship and maybe sort of lookin' around for someone else...Did I do and say those things?...Yes, I did. I am a f--kin' a**hole....That pretty much brings us up to date....What's wrong with me? Seriously. What happened? Why am I doomed to be left? Doomed to be rejected? I need answers... Number five - Jackie Alden. Jackie Alden's breakup had no effect on my life whatsoever. It was a casual thing and I was glad when it ended. I just slotted her in to bump Laura out of position. But now, congratulations, Laura. You made it to the top five. Number five with a bullet. Welcome.