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1* AcclaimedFlop: 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.
2* TheCastShowoff: 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.
3* DawsonCasting: 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 Creator/DennisQuaid playing an early 20s Music/JerryLeeLewis in ''Film/GreatBallsOfFire'', then-33-year-old Gary Busey in ''Film/TheBuddyHollyStory'', wherein he plays Music/BuddyHolly from ages 19 to 22, and then-44-year-old Creator/KevinSpacey playing Music/BobbyDarin throughout his adult life in ''Film/BeyondTheSea'', despite Darin having ''died'' at ''37 years old''.
4** 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.
5** To say nothing of Edith, played by 34-year-old Kristen Wiig!
6---> '''Edith:''' I'm his girlfriend! I'm his 12-year-old ''girlfriend!''
7** 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 [[OlderThanTheyLook pulls it off fairly well]].
8** Likewise, we've also got the similarly-aged Patrick Duffy (58) also playing himself in his early 30s.
9* ExecutiveMeddling: 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 ''Film/SweeneyToddTheDemonBarberOfFleetStreet'' and ''Film/AlvinAndTheChipmunks''.
10* NonSingingVoice:
11** As Jenna Fischer has admitted, she can't sing. Angela Correa dubbed over the songs for the Darlene Madison character.
12** Similarly, the actors playing Dewey's band had to learn how to play their instruments to match the playback.
13* ParodyAssistance: Van Dyke Parks, the composer and lyricist that collaborated with Brian Wilson on the legendary unfinished ''Music/SMiLE'', was asked to co-write and orchestrate "Black Sheep", the movie's ''Smile'' pastiche.
14-->'''[[https://www.theringer.com/movies/2019/5/29/18642513/walk-hard-dewey-cox-oral-history-john-c-reilly-music-biopic-jake-kasdan-judd-apatow Parks]]:''' It required [[SelfParody 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.
15* StuntCasting: Parodied - many of Dewey's buddies are themselves (real life) famous musicians... who are often played by (intentionally) [[QuestionableCasting ludicrously miscast]] famous actors (such as [[Series/MalcolmInTheMiddle Frankie Muniz]] as Buddy Holly and Creator/JackBlack 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 Music/ElvisPresley played by [[Music/TheWhiteStripes Jack White]]). Similar to the DawsonCasting example, they intentionally keep referring to themselves by name to underscore the absurdity.
16-->'''Dewey''': What do you think, George Harrison, [[LampshadeHanging of the Beatles]]?
17-->'''George Harrison''': It's so dark in this tent, you know, it reminds me of when we, the Beatles, the four Beatles--
18-->'''[[Creator/JackBlack Paul McCartney]]''': From Liverpool.
19-->'''John Lennon''': Oh, we are [[ShownTheirWork from Liverpool]].
20* ThrowItIn: 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.

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