Songfacts®:

• The third single from the parody master's sophomore album, "I Lost On Jeopardy" lampoons the Greg Kihn Band's hit "Jeopardy" - which contains the woeful chorus "Our love's in jeopardy" - as a lament from a failed quiz-show contestant. At the time, Jeopardy! was a somewhat nostalgic reference to a defunct game show. The original program ran from 1964 to 1975 with host Art Fleming, but by the time the single dropped, the show was just three months away from being rebooted with Alex Trebek at the helm.
• Greg Kihn, who makes a cameo appearance in the video, took the parody in stride. "It was a vote of confidence," he told The Washington Post. "If you're not well-enough known to be parodied, well, you're just not well-enough known."
• In the music video, directed by Francis Delia (who helmed the Bangles' "The Real World" a year earlier), we find Al on the set of the original game show, complete with Al Fleming as host and Don Pardo as announcer. The singer faces off against a plumber and an architect, both armed with PhDs. He nervously attempts the board's six categories: "TV Themes," "Nuclear Physics," "World Geography," "Food," "Potpourri," and – what should be a stroke of luck for the accordionist - "Famous Accordion Players," but he's no match for his opponents, who successfully answer questions like, "Number of bricks are in the Great Wall of China."
  
  After being berated by Pardo for making himself look like a jerk in front of millions of people and losing out on hot prizes like a lifetime supply of Rice-A-Roni, Al is thrown out of the studio by two stagehands. In a nod to Kihn's "Jeopardy" video, he lands in the back of a convertible driven by the same bride and groom (Kihn) from the original clip.
• The song was featured several times throughout the years on the Trebek-hosted game show, with the contestants being asked to identify the singer of the tune or name the song based on its lyrics. Most failed, but in 2018 this contestant was given a portion of the lyrics and successfully named Weird Al as the artist.
  
  In 2023 it showed up in the Second Chance competition with this clue:
  
  Encyclopedias and a case of Turtle Wax were among the prizes Al didn't win in this song and video that's near and dear to our hearts.
  
  After the contestant answered correctly, host Ken Jennings called the song "the official Second Chance anthem."
• Al actually lost on Jeopardy! when he competed against Harry Wayne Casey (aka KC of KC & The Sunshine Band) and Howard Stern Show producer Gary Dell'Abate on Rock & Roll Jeopardy, hosted by Jeff Probst, in 1999. This song was used during the episode's end credits.