* ActorAllusion:
** Ben Affleck and Liv Tyler had been a couple in ''{{Film/Armageddon}}'' as well. What's more is that Bruce Willis was meant to be in the film AsHimself, and he had also been the lead in ''Armageddon''.
** One of the movies on display at the video store is ''Stealing Beauty'', Liv Tyler's breakout role. Some of Ben Affleck's movies are also displayed such as ''Film/ShakespeareInLove'', ''Film/GoodWillHunting'' and ''{{Film/Phantoms}}''.
* CreatorInJoke: Ollie is named after the ComicBook/GreenArrow. Kevin Smith had written fifteen issues for the comic just before finishing the script.
* PlayingAgainstType: Ben Affleck was at the time best known for being a serious action star. Here he plays an {{Adorkable}} BumblingDad.
* RealLifeWritesThePlot: A scene featuring Ollie and Gertrude's wedding was filmed, but cut from the film after Ben Affleck and Jennifer Lopez broke off their engagement.
* TitledAfterTheSong: The Music/BruceSpringsteen cover of Music/TomWaits' original from ''Music/HeartattackAndVine'' plays over the end credits.
* UnderminedByReality: A bit of an unusual case. Originally the plan was to advertise the movie as being all about the relationship between Affleck and Lopez's characters, making Lopez's [[spoiler:death]] early on a huge shock. But by the time it was released ''Film/{{Gigli}}'' and the general public being utterly sick of them as a couple had killed this plan's viability, so the twist was put right in the trailers, leaving the film with little real identity of its own.
* UnintentionalPeriodPiece: The movie gets dated to the 2000s by having a major character work behind the desk at a video rental store. The store still has a majority of VHS tapes, rather than [=DVDs=], and of course video rental stores went out of business due to the rise of online streaming services. The film also takes place when Creator/WillSmith was at the height of his popularity as a blockbuster star. In TheNewTens he opted for TomHanksSyndrome and a couple of bombs caused his star power to lessen slightly. And if you go meta, the film features Jennifer Lopez and Ben Affleck as a couple, immediately marking it as a product of the 'Bennifer' era.
* WhatCouldHaveBeen:
** Jason Mewes was going to play Ollie's assistant, but was in rehab after he and Kevin Smith had a serious falling out.
** An early idea had Ollie using clips from ''{{Film/Jaws}}'' when he was giving his daughter TheTalk. He wasn't allowed to use footage and so it was dropped.
** While Bart had aways been written with Creator/GeorgeCarlin in mind, Carlin had originally asked Smith to write him his dream role: a clergyman who strangles six children. When Smith sent Carlin the script, Carlin, true to form, called him the next day asking [[CrossesTheLineTwice why his character doesn't strangle the little girl]].
** One cut of the scene where Ollie finds out that Gertrude died in childbirth ended with him vomiting on the floor because Ben Affleck was so LostInCharacter that [[EnforcedMethodActing the heavy emotion of the scene began to make him physically ill]]. It was rejected when [[{{Narm}} test audiences started laughing]].
** The film was originally going to be set in the late 80s and Ollie would have badmouthed Bruce Willis. When a deal with Bruce Willis couldn't be secured, it was changed to Will Smith.
** Creator/ElizaDushku was the first choice for Maya, but Kevin Smith changed his mind. Upon seeing Eliza at only 5"4', he realised she would look far too young to be Ben Affleck's love interest.
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