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1* CrossDressingVoices: Jason Levine sings the female parts on "Strange Disease" and "Wild Thing/Poor Boy" in a falsetto.
2* {{Defictionalization}}:
3** For a time, searching for www.nevergetoveryou.com would redirect one to a page on the band's official website. Both are now defunct.
4** The concert setup for the "www.nevergetoveryou" video eventually became the band's real-life tour setup, with Jay and James performing in-character as Simon & Milo atop giant busts of the characters.
5* EarlyBirdCameo: Stacy The Computer, who would become a recurring character on the ''Saturday People'' album, first appears in the video for "Wild Thing/Poor Boy."
6* FakeNationality: A pop duo consisting of a Brit and a [[WhatTheHellIsThatAccent vaguely Eastern-Europian guy]], as portrayed by two Canadians.
7* HeAlsoDid: Jay and James produced and co-wrote Fefe Dobson's debut SelfTitledAlbum, as well as "Get Down" for the BoyBand [=b4-4=].
8* KeepCirculatingTheTapes
9** The music video compilation "Simon & Milo present Prozzäk's Hot Show" has never been released on DVD. Bits of it are often found floating around Website/YouTube.
10** "DJ-J-Vox" and it's remix were only ever released on the band's Website/MySpace page.
11* NoBudget: It's clear from the designs of the album, the LimitedAnimation in the "Love Me Tinder" video and the minimal production that ''Forever 1999'' was more a passion project by the band than an investment by a major label.
12* NoExportForYou: Saturday People was never physically released outside of Canada due to poor sales.
13* OfficialFanSubmittedContent:
14** The verses for "Infatuation" were written by a contest winner.
15** The single cover for "Baby I Need Your Love (Pussy Cat)" and the animations counting down the days to its release on Facebook were created by a different contest winner.
16* TechnologyMarchesOn
17** The lyrics of "Sleep With Myself" describe intimacy being lost in the digital age with "fax machines" being mentioned in the same breath as computers.
18** While the lyrics of "www.nevergetoveryou" remain topical in an age of social networking and online dating, the title grows more and more dated as the internet becomes less of a spectacle and websites are succeeded by apps.
19* WhatCouldHaveBeen: A Simon & Milo cartoon was planned for Creator/DisneyChannel in the early 2000s, with ''Ready Ready Set Go'' and the band's title song for the channel's MadeForTVMovie ''Film/GetAClue'' testing the waters with their audience. However, Jason Levine wound up clashing with executives over [[AnimationAgeGhetto what they considered "age appropriate" for Disney's core audience]] and the project fell through, though [[https://archive.org/details/simonandmilo_202107/mode/2up storyboards for a pilot episode where made]].
20* WordOfGod: Jason Levine claims that Simon lacks a neck so that there can be [[ShootTheShaggyDog one more thing burdening him]].
21* WriteWhatYouKnow:
22** Jason Levine. "Everything that happened to Simon happened to me."

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