The Random Game is (was) an area of Heckler's Online on America OnLine. Several winning entries are interspersed within this entry.

The cool thing about Star Wars is that Princess Leia never wore a bra. (Tocadisco)

It began as a blank CGI form in which you wrote something. Anything. As long as it was clever. Winners were chosen and awarded tokens, which were redeemable for prizes.

The shortest sci fi story ever written: Time ended. Yesterday. (TDodge8353)

Later, a new format was introduced: a simple message board. This was met with much resentment. We threatened to go on strike, and then we realized that it wouldn't work.

Goo's 1998 Predictions: After tiredlessly draggin his ass across, and eating portions of, the White House lawn, the Clintons' new pup Buddy will come inside and vomit on the carpet of the Oval Office. USA TODAY will publish a page-one, full-color graph analyzing the event. (SGood42)

Much later, when HO was purchased by Playboy Humor, they dropped the game entirely. HOWEVER, they never removed the message board. Even though the reward was gone, the community thrived, reveling in its ability to use copious profanity.

A friend told me yesterday that I talk behind people's backs too much. Oh well, he's a real loser and no one really likes him anyway. (BrianJ718)

Eventually, however, the board died out (despite a brief attempt on the part of HO to revive it).

My cat keeps licking the window...he must have mistaken it for his balls. (SoupEater)

Most of us migrated to Jimbo's World (another online forum), but we generally still keep in touch.

:::throws a sock at the fan::: I could do this for hours
::fills sock with whip cream and throws it at fan::: I could do this for days!
:::puts cherries in sock with the whip cream and throws it at fan::: I could do this for at least a week!
:::puts a banana with the cherries and whip cream in the sock and throws it at fan::: I could keep doing this all month!
:::puts a huge hunk of ice in the sock with the banana cherries and whipped cream and throws it at fan::: Ah crap, I broke the fan, I can't do this anymore! (CowKosmo)

Most of the posts are lost in the ripples of history, but some people still maintain limited archives.

I think the best way to convince guards to let you out of an insane asylum is to scream "I'M NOT CRAZY!", like, a lot. And it helps to wiggle around and struggle with your straightjacket. (Mr Onliner)

Fans of "Deep Thoughts with Jack Handey" and Steven Wright will probably recognize the general style.

Scary thought: When I get old, will there be "classic rap" radio stations? (RavenWord7)

addendum in re: mooky
The Random Game (the .org one, which is the latest incarnation of my above post) is far more fun to play. Suck it, bitch.