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  • Acclaimed Flop: One of the few parody movies released Post-Scary Movie to actually do pretty well critically, but releasing it during a crowded Christmas season killed the chances of it actually turning a profit.
  • The Cast Showoff: John C. Reilly, already an established singer, is the only actor in the movie who wasn't dubbed and the movie clearly enjoys showing off his pipes. He's also noticeably the only one who doesn't flub playing his instrument.
  • Dawson Casting: Parodied, given the trend of several biopics (especially musical ones) where this happens, such as then-39-year-old John Goodman playing a teenage Babe Ruth in The Babe, then-34-year-old Dennis Quaid playing an early 20s Jerry Lee Lewis in Great Balls of Fire!, then-33-year-old Gary Busey in The Buddy Holly Story, wherein he plays Buddy Holly from ages 19 to 22, and then-44-year-old Kevin Spacey playing Bobby Darin throughout his adult life in Beyond the Sea, despite Darin having died at 37 years old.
    • John C. Reilly, aged 42 at the time, plays Dewey as a fourteen-year-old and keeps mentioning his age just to underscore the ridiculousness.
    • To say nothing of Edith, played by 34-year-old Kristen Wiig!
      Edith: I'm his girlfriend! I'm his 12-year-old girlfriend!
    • 59-year-old Cheryl Tiegs plays herself in her early 30s as Dewey Cox's wife (in the unrated version). Still, it can be argued that she pulls it off fairly well.
    • Likewise, we've also got the similarly-aged Patrick Duffy (58) also playing himself in his early 30s.
  • Executive Meddling: Sony cut over twenty minutes (including an entire subplot that was shown in the trailers) from the film before it opened. They also released it in a crowded Christmas season, letting it die against the also music-themed Sweeney Todd: The Demon Barber of Fleet Street and Alvin and the Chipmunks.
  • Non-Singing Voice:
    • As Jenna Fischer has admitted, she can't sing. Angela Correa dubbed over the songs for the Darlene Madison character.
    • Similarly, the actors playing Dewey's band had to learn how to play their instruments to match the playback.
  • Parody Assistance: Van Dyke Parks, the composer and lyricist that collaborated with Brian Wilson on the legendary unfinished Smile, was asked to co-write and orchestrate "Black Sheep", the movie's Smile pastiche.
    Parks: It required the ability to self-criticize and to be the victim of my own joke. And I was put in that position. I was delighted to do it.
  • Stunt Casting: Parodied - many of Dewey's buddies are themselves (real life) famous musicians... who are often played by (intentionally) ludicrously miscast famous actors (such as Frankie Muniz as Buddy Holly and Jack Black as Paul McCartney), or famous musicians being played by other actual musicians... who are absolutely at the other side of the musical style (such as Elvis Presley played by Jack White). Similar to the Dawson Casting example, they intentionally keep referring to themselves by name to underscore the absurdity.
    Dewey: What do you think, George Harrison, of the Beatles?
    George Harrison: It's so dark in this tent, you know, it reminds me of when we, the Beatles, the four Beatles—
    Paul McCartney: From Liverpool.
    John Lennon: Oh, we are from Liverpool.
  • Throw It In!: All over the place; most notably, when the band confronts Dewey over his shitty treatment of them, Tim Meadows saying "And you never ONCE paid for drugs! Not once!" was only one of several lines in the script, but he decided to just keep insistently repeating it. The result became one of the film's most quoted scenes.
  • What Could Have Been:
    • Jake Kasdan mentions in the DVD commentary that he had written a few scenes to show that Dewey's addictions would've eventually led to him getting hooked on heroin: he mentioned one scene where Dewey performed with a needle stuck on his arm, and another where he would've accidentally invented Grunge during the first time he did heroin (as a call back to the scene where he accidentally invents punk rock the first time he does cocaine). John C. Reilly notes that with the exception of Trainspotting "it's really hard to make heroin addiction funny".
    • The scene with Dewey meeting The Beatles was supposed to also have Stephen Merchant play their manager, Brian Epstein. The role was cut because he already had a vacation planned.
    • The LSD trip scene was originally entirely different: instead of a Yellow Submarine homage, it was a more straightforward retelling of the scene where Dewey killed his brother. It came off as MUCH more scary than funny, leading to the aforementioned Trippy Cartoon
    • The audition scene with "That's Amore" was originally "Moon River", but Kasdan later discovered that "Moon River" came out in 1961 (seven years after the scene is supposed to be set) and changed it.
    • The Line-O-Rama feature on the DVD had an alternate take on the last "you don't want none of this" scene: rather than medication for erectile dysfunction, Sam was going to be smoking a blunt and saying that he was "going back to his first love".

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