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Celebrity Jeopardy! refers to any one of a number of episodes or tournaments of the popular television game show Jeopardy! in which the contestants are celebrities. Each celebrity chooses a charity to sponsor, and that charity is the recipient of the particular celebrity's winnings. Typically, the charity is guaranteed a certain amount (at one time, $5,000 for a loss; $10,000 for a win) unless the celebrity earns more than that amount. Also, the rules are usually relaxed so that, for example, celebrities are not penalized for forgetting to respond in the form of a question.
Celebrity Jeopardy! also refers to a popular recurring sketch on Saturday Night Live which parodies the above. The cast members appearing mostly vary, but Will Ferrell (as Alex Trebek) and Darrell Hammond (as Sean Connery) are almost always featured.
The sketches always begin during what is apparently the second half of a round of Jeopardy!, and two of the "contestants" have somehow attained very high negative scores while another "leads" with a score of zero. Trebek, being portrayed as the beleaguered straight man, attempts fruitlessly to manage the contestants, who are over-the-top caricatures of other celebrities. The contestants blatantly misinterpret questions, misread topic titles (S-Words becomes Swords, for example), and in general display high levels of neuroticism and incompetence. Meanwhile, Trebek insults the contestants, is bombarded with sophomoric insults from Connery, and eventually finishes with giving up on the scripted questions and delivers a childishly simple "Final Jeopardy!" question (e.g. "Things You Like", "Don't Do Anything"), which of course is always botched by the contestants.
The sketch was apparently retired on Will Ferrell's own retirement as a regular SNL castmember in 2002. The final sketch featured the real Alex Trebek in a cameo appearance.
05-18-02 - Sean Connery, Dave Matthews, Björk - I have a Chardonnay
09-29-01 - Sean Connery, Chris Tucker, Anne Heche - Hor-semen
02-08-01 - Sean Connery, Ozzy Osbourne, Martha Stewart - Don't do anything
12-16-00 - Sean Connery, Robin Williams, Catherine Zeta-Jones - Anal Bum Covers
04-15-00 - Sean Connery, Keanu Reeves, Hilary Swank - Below Me
10-23-99 - Sean Connery, French Stewart, Burt Reynolds - Turd Ferguson; A Petit Dejeuner
03-20-99 - Sean Connery, Calista Flockhart, Nicolas Cage - The Pen-is Mightier
10-24-98 - Sean Connery, Adam Sandler, Tom Cruise - Where are you?
05-09-98 - Sean Connery, Minnie Driver, Jeff Goldblum - Therapists
10-04-97 - John Travolta, Michael Keaton, Burt Reynolds - Chinese whore, ASIA
05-10-97 - Marlon Brando, Phil Donahue, Burt Reynolds - Name this color, the current year
12-07-96 - Sean Connery, Burt Reynolds, Jerry Lewis - "S" Words