- Actor-Shared Background: Vince Vaughn's character lives in Chicago, as does Vaughn himself.
- Box Office Bomb: Budget: $70 million. Box office: $48,475,290 (domestic); $21,246,676 (international).
- Completely Different Title: The German for dilemma is "dilemma". So, naturally, in Germany, The Dilemma is shown as Dickste Freunde — which means Fat Friends. Or less literally Best Friends.
- Distanced from Current Events: Trailers for the film were pulled due to Vince Vaughn's character describing hybrid cars as gay ("but not in a homosexual way") after a rash of gay teen suicides.
- Star-Derailing Role: For Vince Vaughn. He forced many rewrites onset, took over creative control from director Ron Howard, and defended his character's homophobic comments. Consequently, audiences stayed away.
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