as cool as the other side of the pillow 

About as cool as a person can possibly be, sort of like James Dean or someone like that, but even cooler. Possibly originated from SportsCenter. Has nothing to do with temperature.

I was as cool as the other side of the pillow back in high school. I used to sit in the back of the class in my leather Harley Davidson jacket and sunglasses, smoking my Marlboro Reds and drinking whiskey out of a silver flask. I'd just sit back there, all laid back across the seat, with my arms around the two hottest girls in the school. The teacher would tell me to put my cigarette out and stop drinking, and I would blow smoke in her face and say, "Make me." But she wouldn't make me because I was just too cool.
No, not really, actually I was a fucking dork who watched Star Trek marathons and still haven't lost my virginity except for my dog that one time.
No, just kidding again, I was pretty normal, but I always used to look at the other side of the pillow and wished that someday I could be that cool. Sadly, it never happened.

as cool as the other side of the pillow by Nick D October 13, 2003

cool as the other side of the pillow 

A state of being very calm and collected, rarely freaking out or becoming over-emotional, and generally well-respected by the majority of people. May have originated from ESPN's SportsCenter.

Man, back in high school I was the shit. I used to ride up about 10 minutes late every day on my Harley-Davidson in my leather jacket and sunglasses. I'd walk into class and take my usual seat in the back of the room, where the two hottest girls in the school were waiting for me. Then I'd light up a cigarette, Marlboro Red of course, lean back in my seat to where I was almost lying down, and put my arms around the girls. If the teacher told me to put out my cigarette, I'd laugh and say "Make me." She wouldn't of course because I was too cool to not smoke. Yeah, I was about as cool as the other side of the pillow.
No, actually I was a nerd who watched Star Trek marathons and wrote code for Mac OS 9 at age 12.
No really, I was always pretty normal, but I always used to look at the other side of the pillow and wished I could someday be that cool.

cool as the other side of the pillow by Nick D October 20, 2003