You Don't Know Jack: The Ride is a 1999 trivia party game developed by Jellyvision and published by Sierra On-Line. As the third installment in the popular You Don't Know Jack series, it trades the traditional television studio setting for a theme park, framing each round as a roller coaster ride where players answer absurd, pop-culture-laced multiple-choice questions. The game supports up to three simultaneous players using a shared keyboard, with buzz-in mechanics, point-stealing screw opportunities, and the series' signature blend of biting humor delivered by the sardonic host, Cookie Masterson. Released for Windows 95/98, The Ride continued the franchise's tradition of mixing genuinely challenging trivia with irreverent comedy and quick-fire pacing, making it a staple of late-'90s PC party gaming.
Box Art
The Vault · 1999
You Don’t Know Jack: The Ride
The trivia party game gets a theme park season pass.
You Don't Know JackWindows 95/98PartyTrivia
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HardwareHow to Play TodayYour options for running this game in 2026
Original Hardware
Original CD-ROM copies surface on eBay and in thrift stores. Requires a Windows 95/98 machine with a Pentium processor, 16 MB RAM, and a 4× CD-ROM drive.
Modern Re-release
Part of the You Don't Know Jack bundle on GOG.com, fully compatible with modern Windows.
Emulation / Other Options
The game runs well in virtual machines like VMware or VirtualBox with a Windows 98 guest, or via DOSBox with Windows 95/98 installed. Mount the CD-ROM image and ensure sound drivers are configured for the era-appropriate audio.