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An adjective meaning "scatter-brained, not quite right in the head." Derived from game-show host Chuck Woolery.
"He used to be sensible, but he's gotten woolery with age."
woolery by Ignatzz August 20, 2019

Woolery left Wheel 

A phrase that started out on alt.tv.game-shows in the days when the group wasn't troll infested. Used as a retort towards people who are telling other members old news that they already knew.
Poster 1: Did you know, Regis hosts Millionaire?
Poster 2: Well duh! Woolery left Wheel!

Chuck Woolery 

A sexual act requiring the insertion of both the index finger and middle finger into the vagina, while inserting the pinkie and ring finger into the anus. In some circles this has been more commonly known as "The Spocker". The moniker used here relates to the catch phrase "We'll be back in two and two". As you are giving the willing recipient "Two and Two".
As commonly used "I've been known to Chuck Woolery a lady every now and again" or "This one girl had been shockered before, so I decided to introduce her to my man Chuck Woolery".

"On my dating game, I pull the Old Chuck Woolery, and I'm guaranteed a second date"
Chuck Woolery by TheycallmeCoxie December 1, 2009

Sloppy Woolery 

the act of putting on thick black rimed glasses
and releasing fecal matter upon them until they overflow on to your partners breasts then licking them off while wearing a cheetah leotard dancing to earth,wind and fire.
first ever attempted sloppy woolery was on his worst trumpet players.
to epic win to explain try on your partner she will enjoy the sloppy woolery .

Chuck Woolery 

Taking two dumps before 2:00 pm, as in Chuck Woolery's catch phrase "We'll be back in 2 and 2."
Dan: I really need to crap. It's my second one and it's only 1:00.

Mark: Way to pull off the Chuck Woolery!
Chuck Woolery by RabbiDan August 27, 2009
A marijuana joint.

Most notably used in lyrics by the Beastie Boys and NWA.
I rolled me a wooler as I decided whether to crack open the Brass Monkey or the eight ball.
wooler by Andrew S April 8, 2004