* ActorAllusion:
** Creator/BenAffleck and Creator/LivTyler had been a couple in ''{{Film/Armageddon}}'' as well. What's more is that Creator/BruceWillis 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}}''.
* BoxOfficeBomb: Budget, $35 million. Box office, $25,268,157 (domestic), $36,098,382 (worldwide). The second film to star Creator/BenAffleck and Creator/JenniferLopez flatlined in the wake of their disolved relationship and their disastrous [[Film/{{Gigli}} first film from the previous summer]]. Fans of Creator/KevinSmith were turned off by its mainstream approach.
* CreatorInJoke: Ollie is named after the ComicBook/GreenArrow. Creator/KevinSmith had written fifteen issues for the comic just before finishing the script.
* DeletedScene: A scene featuring Ollie and Gertrude's wedding was filmed, but cut from the film after Creator/BenAffleck and Music/JenniferLopez broke off their engagement.
* PlayingAgainstType: Creator/BenAffleck was at the time best known for being a serious action star. Here he plays an {{Adorkable}} BumblingDad.
* PlayingWithCharacterType: Creator/GeorgeCarlin's Bart is still a cantankerous "old fuck," but one with a gentle soul who loves his family.
* RealLifeRelative: Creator/KevinSmith's wife appears as a receptionist, while his daughter is an extra.
* RoleEndingMisdemeanor: Jason Mewes was going to play Ollie's assistant, but was in rehab after he and Kevin Smith had a serious falling out.
* SoMyKidsCanWatch: Creator/KevinSmith made the film because he'd just had a daughter and wanted to make a movie that wasn't filled with crude humor. Unfortunately, a lot of his fans were angered by their hero "going soft," and he was forced to make a return to form. Watching the movie knowing that it was made for and about Smith's daughter does make the movie much sweeter, though.
* 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. (AvertedTrope since the film was originally set in the 80's, with Ollie loosing his job by trashing Bruce Willis' singing aspirations.)
* WhatCouldHaveBeen:
** 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 Creator/BruceWillis. When a deal with Bruce Willis couldn't be secured, it was changed to Creator/WillSmith.
** 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.
* WriteWhatYouKnow: The film was based on Creator/KevinSmith's experiences with fatherhood.
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