GameShow created in 1987 by [[Series/{{Tattletales}} Bert Convy]] and Burt Reynolds. In it, two teams, each comprising two celebrities and a contestant, competed in what basically amounted to televised ''Pictionary'' (never mind that there have been two different game show versions of ''Pictionary'' proper). It consisted of three rounds wherein a team member attempted to convey a given answer (usually a person, place or thing) by drawing it. At the 30-second mark a doorbell sound effect was heard, and the team member doing the drawing could opt to pass the marker to the next person in line. A correct guess earned $200 (or $100 if the marker was passed) for the team in play; if they failed to guess, the opposing team could take a guess for $100.

Both contestants competed in a BonusRound called the "Speed Round". Here, both contestants attempt to draw as many one-word answers as possible within 90 seconds, earning $100 for every correct guess from their teammates but allowing only two passed answers. Whoever had more money at the end of this round won the game and a $1,000 bonus ($500 apiece for a tie). Towards the end of the daytime version, a new endgame was used, decreasing the speed round to 60 seconds and $50 a word: the winner had 90 seconds to draw as many one-word answers as possible. The first word was worth $50, then doubling with each successive answer; there was no limit to the winnings. The syndicated version's last season adapted this format (along with a 10-day returning champion format), but limited it to seven words, with the seventh bumping the money from $1,600 to $5,000.

The show aired in two different formats, both of which debuted on the same day in 1987 a daytime version on Creator/{{NBC}} hosted by Vicki Lawrence, and a nighttime syndicated version hosted by Bert Convy. The daytime version was canned in 1989, and Robb Weller took over on the syndicated version for the 1989-90 season (Convy left to host ''3rd Degree!'', which he and Reynolds also produced).

The Creator/DisneyChannel produced its own version, called ''Teen Win, Lose, or Draw'' and hosted by Marc Price. This version began in April 1989 and outlasted the syndicated run, airing until 1992. Disney Channel revived the series as ''Disney's Win, Lose or Draw'' in early 2014 with Justin Willman as host.
!!GameShow Tropes in use:
* BonusRound: An unusual variation, in that both teams are still in play. Played straight with the "Doubling" round.
** Also played straight in the 2014 revival with only one team in play.
* Personnel:
** TheAnnouncer: Gene Wood, a friend of Bert, announced the Convy version. Bob Hilton announced on the daytime show and occasionally filled-in on the nighttime version; Johnny Gilbert was an occasional substitute as well.
*** Brandy Brown, Chase Hampton, and Tiffini Hale rotated duties on the first season of ''Teen''. Mark L. Walberg became the permanent announcer when the show moved to California in September 1990.
** GameShowHost: Bert Convy, Robb Weller, Vicki Lawrence, Marc Price. The last three have never helmed a game show before or since, although Lawrence had been a celebrity player on several games. Justin Willman hosts the 2014 revival.
** StudioAudience
!!This show provides examples of:
* AlohaHawaii: A week's worth of the syndicated version was played on an outside stage in the 50th state, with A-list celebrities Burt Reynolds, Jim Nabors, Carol Burnett and Loni Anderson. Instead of the doorbell, a shell horn was blown to signal the switch-off point.
* CelebrityEdition: The 2014 Disney Channel revival features current Disney Channel stars participating with regular contestants in every episode.
* ColorCodedForYourConvenience: Markers of various colors were provided to help players with answers to convey such as "Jolly Green Giant" and "Devil with the Blue Dress On".
* DistaffCounterpart: Vicki Lawrence in daytime, Bert Convy (later Robb Weller) in Syndication.
* FreudianSlip: On one episode, Bob Hilton accidentally introduced Bert Convy as "Bert Lawrence".
* GameBreakingBug: An unusual trope for a live-action game show: There seems to be a lot of miscommunication between the judges in terms of what exactly is allowed and whether or not the contestants are able to guess the word in time.
* OpeningNarration: Convy's version used the following: "Welcome to the quick draw game that everyone can play! It's ''Win, Lose, or Draw''! Come on in and join our host, Bert Convy! With Bert's guests...(''announcer lists off each celebrity partner, as a caricature of each is revealed on the sketch pad'')...And one more time, Bert Convy! (''caricature of Bert is revealed'')"
* {{Pilot}}: A pilot was taped on November 2, 1986 with Bert Convy as host, and the celebrity guests being Loni Anderson and Betty White vs. Tony Danza and Burt Reynolds. It aired as a special sneak preview episode.
* PlayingPictionary: The entire premise.
* PunnyName: Pretty obvious.
* RearrangeTheSong: The Weller version used a mellower remix of the theme.
** The Hawaiian episodes featured a version of the theme as Don Ho might have played it.
* ShoutOut: One episode of the Weller version had his caricature drawing consist of him being CoveredInGunge by [[Series/DoubleDare1986 Marc Summers]].
* TransatlanticEquivalent: It was exported to Britain in TheNineties.