Season 16 of Jeopardy! kicks off on September 6, 1999.
The opening credits were changed to a new flyover past the Sony Pictures Studios complex. We zoom out on a TV tube shape to show various photographs from the show on some TV tubes, which moves from right to left. As this happens, gold letters pop in one by one to spell out Jeopardy!, then one final TV tube floats from the right and zooms in to reveal the 1996-2002 set.
At the beginning of this season, Jeopardy! and its sister show Wheel of Fortune are now presented in WebTV interactive. This was done because WebTV wanted to play online with Jeopardy! and Wheel of Fortune.
This is the last season to have Johnny Gilbert's opening catchphrase "Now entering the studio are today's contestants", in which the contestants entered the studio during their introductions. Starting in Season 17, the contestants no longer entered the studio at the beginning of the show, they are now standing behind their podiums.
This is also the last season, in which Johnny Gilbert said "From the Sony Pictures Studios, this is Jeopardy!" at the start of each episode.
This is also the last season, in which Jeopardy! announcer Johnny Gilbert signs off at the end of each episode. Starting on January 3, 2000, episode, he no longer signs off at the end of each episode.
On the December 8, 1999, episode, Alex Trebek explains to the viewers at home of what the crew does during the commercial break, just right before the Final Jeopardy! segment.
It includes two contestant coordinators, a stage manager, and an electronic score keeper.
Harry Friedman became the executive producer.
On the season premiere week, the Game Show Network logo is changed to the "Ball Maze" logo with the voice-over saying "Why just watch television when you can play from home? Game Show Network! Buzz your cable company to get in the game!". No music plays at all during the plug.
In the late October 1999 episode, Eddie Timanus became the first blind contestant to appear on the Jeopardy! set. During his appearance, the contestants are standing at their podiums for the second time. This change becomes permanent next season.
The weeks of the November 8, 1999 episode, and the November 15, 1999 episode are taped at Madison Square Garden in New York City.
November 8 'til November 12, 1999, was the semi-final and final episodes of the Teen Tournament, and from November 15 'til November 19, 1999, was Celebrity Jeopardy!.
The College Championship was held in February 2000 in Sony Pictures Studios, Sound stage 10 with a college-themed set. Janet Wong from Drew University won the college tournament of $50,000, a Volvo S40 sedan followed by a college trophy.
By the December 27, 1999 episode, the Jeopardy! Online logo changed to a "Play Online and Win" logo. The logo is in a blue text on a yellow oval. The music from the first logo is remixed, with some parts added to it as the letters of "Play Online and Win" pop in one by one.
Johnny Gilbert signs off for the last time on the December 31, 1999 episode. Therefore, his voice won't be heard starting on January 3, 2000, episode.
On the February 10, 2000, episode, Johnny Gilbert appeared on camera after reading the clues for a Poetry category.
On the May 15, 2000, episode, the Tournament of Champions is held in Atlanta at the Atlanta Civic Center.
During the first quarterfinal games of that episode, after Johnny Gilbert said, "From Atlanta, Georgia, this is the Jeopardy! Tournament of Champions!". Then five seconds later, after the audience applause, then he introduced Alex Trebek on stage first before introducing the contestants. This is because Alex Trebek wanted to explain to the viewers at home that this is the first time that they taped the Tournament of Champions on the road.
Then they showed the fifteen champions on the game board followed by applause.
This year's Tournament of Champions included two Teen Tournaments, 2 College Championships, and 11 5-time champions.
It was the last time, the Teen Tournament victors are eligible for the Tournament of Champions.
The first three competed in the first match with Johnny Gilbert's introduction followed by the game.
The dollar figures for the first round on the game board was already set up during the introduction. They didn't pop in. They did it like that for Season 25. This was the last time that Johnny Gilbert announced how much winnings these champions earned on their last appearance of the show during the quarterfinal introductions after their name.
Robin Caroll, from Marietta, Georgia, won the $100,000 Tournament of Champions in her hometown.
On the June 30, 2000, episode, Alex Trebek brings his kids, Matthew Trebek, and Emily Trebek, onstage with him at the beginning of this episode.
On the July 5, 2000 episode, Johnny Gilbert accidentally announced himself as "Glen Trebek".