Rollerskates made out of ASCII art.
The ASCII characters keep falling off my lollerskates.
by ??^?? June 17, 2008
What you ride when you fail at life.
Chris Rock likes to ride lollerskates all night long.
by The Carter III November 29, 2010
A skate designed by the notorious lol inc. Few pictures of the skate have been released, most likely because only two prototypes of the skate are believed to exist. There had been an auction for one such Lollerskate on E-bay several months back. Both the seller and the bidder of this Lollerskate was unable to be tracked. The latest rumor has it that the Lollerskate has been sold to the government in an attempt to provide U.S. troops with cheap, comfortable, and efficient transportation, but I doubt that we'll ever know the truth. As to what a Lollerskate actually can do is also a mystery, although Jeffrey Lamaou certainly has an idea as to the properties of the Lollerskate as made apparent by his May, 2004 statement, "The Lollerskate will soon see mass-marketing and production by the year 2023, and it will go hand in hand with flying cars." With the limited documentation that's available to the public regarding the Lollerskate, the only concrete information is that it will be released with the price tag of $100-250 dollars per pair. With such an unimaginably low price for such a woundrous product, I for one am eager to ascertain its details. More as it develops.
Yeh fo' sho nigga, dat cadillac makes 1 hella ride but it ain't no fuckin' lollerskate ya know wut im sayin'?
by wtf October 18, 2004
When one gets an immense amount of lag in WoW and trys to loot a monster, then slides around on his knees without any movement animation.
Wow! Check it out, the horrible lag has made me lollerskate for the 4th time in a minute.
by Insomne February 27, 2005
The word of gods, and those that are righteous. Usually used in the context of applauding a totally Schlagging thing. see Schlag

Be forewarned... usage of this word may raise your douche-o-bag meter.
DOOD! LOLLERSKATES!!! WANNA TOUCH MY SCHLAG!?!

-or-

DOOD! THAT GETS 15 LOLLERSKATES!
by The-Cabbage-Patch-Snack April 23, 2005
A lollerskate is a type of point/award that can be given to any one person at random. Depending on how totally awesome the action involving the person is, a certain number of lollerskates will be awarded to that person. 50 lollerskates is the highest number of lollerskates that can be awarded and is considered a great honor, an even greater honor when combined with a number of Schlags.

Also: A word used by only the most worthy of worthy people who have had sex with an infinite amount of hamsters and people of the same sex. The hamsters however, have to be in the right season and must have a dichotomous expanding colon the size of 15 landladies. This word can only be used in the context of something so funny, people's guts will literally fly out of their owners.
Congrats! You recieve 50 Lollerskates on the acquisition of your new car! And a Schlag!

"lollerskates!!!!!!"
by Ric The Spic April 23, 2005
One of them niggas that be running around the bend sippin on 40's like the old days.
A yo I just seen that bitch ass lollerskate down this way.
by Jordan January 17, 2004

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