Groundhog Day and Rushmore are two of my all-time favs with Bill. A little trivia: the Xena episode, 'Been There, Done That' was written to be just like Groundhog Day as Sam Raimi and Rob Tapert thought it was the best movie of the 90s.
I've seen that one (my wife was a big Xena fan), and I thought at the time "That's a video game premise, just like GHD!"
Actually, I haven't played any video games for years, but they've finally gotten so well done that they're pulling in more revenue than movies with the younger set.
One of my sons got me a copy of Half-Life2 for Christmas, and I finally completed it yesterday. There were a number of segments in that game that I had to run over and over, seemingly endlessly, before I got all the steps right and was able to advance.
That game is a real white-knuckle experience if (like me) you're afraid of heights!