- Casting Gag: The two actors who play Harold's coworkers had previously appeared together in a series of commercials for the Sonic Drive-In restaurant chain.
- Playing Against Type: Will Ferrell movies that came out around this time were defined by wacky hijinks (Step Brothers, Talladega Nights: The Ballad of Ricky Bobby, and so on). Ferrell is considerably more restrained, quiet and introspective in this movie, with his most over-the-top moment being when he has his Rage Against the Author moment. Otherwise, he plays the part of a man hearing his own life being narrated and his impending death as straight as he can, and it's surprisingly poignant when he has his moments of tragedy, terror and wonder.
- Technology Marches On: Harold relies on his wristwatch to maintain a strict schedule and a slight error in time setting, because someone else's watch was incorrect, throws him off completely. Since this film, cellphones and smartphones have become ubiquitous and these devices are centrally synchronized, meaning there's little chance that Harold will be told the wrong time if he were to ask someone.
- Tom Hanks Syndrome: This is one of the first dramatic roles in Will Ferrell's career and since this film, he's turned in a series of well-received dramatic indie roles alongside his usual comic fare.
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