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.

by Nick D October 13, 2003

Going "Behind the Pillow"

When a couple puts a pillow in front of their faces to shield others from seeing them makeout.

Hey, did you see Marisa and Chris going "behind the pillow" while we were watching Drag me to Hell?

by insanebolt108 May 27, 2010

Kick the Pillow

1: to warn a person about something after it is far too late for them to do anything about it

2: to attempt (generally poorly and without success) to cover up something (often done at the time of the commission of the act which is to be covered up or immediately after)

Etymology: "Kick the Pillow" is derived from a practice of Feudal Japan. It was considered dishonorable to kill a sleeping enemy, so a warrior would kick his enemy's pillow in order to wake him just before chopping off his head. This allowed the warrior to maintain his honor (at least by the literal letter of the rules) while preserving the advantage of taking an enemy completely unawares.

1: (Historical) The Japanese sent a telegram to their embassy in Washington D.C warning of their impending attack on Pearl Harbor, which was intended to be delivered to the US Government just minutes before their attack began. Unfortunately the ambassador was too slow in decrypting the message, and the US had already decalred war on Japan before he finished, so it was never delivered.

2: "I'm back. Gotta love taking long lunch breaks."
"Yeah, well the boss wants to see you in his office. Last week I heard him saying he was thinking about firing you for taking extended lunch breaks."
"Oh, fantastic! Thanks for kicking the pillow, jerk!"

3: "Surprise! My mother is moving in with us! She just pulled into the driveway."
"Thanks for kicking the pillow, honey."
(Guess who's not getting laid until she moves out?)

4: "You slept with her?!"
"Well... I did say I wanted to talk about seeing other people."
"Oh yeah, good job kicking the pillow."

by IRONSWORD1 May 14, 2005

whats under the pillow

its a question bloods ask new coming gang members of their gang to make sure there down. They ask whats behind the moon, whats under th bed, and whats in the closet

whats under the pillow? the red bandana

by dk65 February 19, 2010

to bite the pillow

To have unlubricated or painful anal sex (usually referring to gay sex), referring to the face-down-ass-up position of the recipient and the need to bite something to keep quiet.

#1 "So, did you guys do it last night?"

#2 "Yeah, but he had no lube, so I had to bite the pillow"

#1 "Ouch"

by RCAP March 30, 2011

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.

by Nick D October 20, 2003

cooler than the other side of the pillow

This phrase is an adjective used to describe someone who's demeanor is so cool that if you don't like them, there is something wrong with you; a literal description based on waking up at night, flipping your pillow, and the coolness making you feel so good you fall back to sleep.

Chris? Oh that dude is the shit! He's cooler than the other side of the pillow.

by Cunninglinguist69 September 9, 2008