- Humble Beginnings: Some of the Promoted Fanboys who got their start here include: Kira Buckland, sonicmega, Egoraptor, Smosh, xKore, FDA, etc.
- Newbie Boom: When Tumblr issued a ban on all NSFW content in November-December of 2018, Newgrounds found itself the refuge for artists driven off the site, hitting record highs in active users. So many people joined, that the servers crashed trying to keep up.
- Old Shame: The period in the early '00s right after the dot-com bubble burst, when funding and advertising for internet ventures pretty much dried up almost entirely. Around 2002, they had to start running ads for porn sites in order to pay the bills and update their aging servers, something Tom Fulp regards as one of the darkest moments in the site's history.
- Screwed by the Lawyers: Around 2015, various older movies and games began to be removed to avoid copyright claims against the site and to encourage the use of original music from the Audio Portal.
- Almost every Super Mario related game was removed during the period where Nintendo sent out Cease and Desist orders to numerous websites hosting Super Mario games before the release of Super Mario Maker.
- Early on in the site's history, a movie called You're a Raging Psychopath Snarlie Brown! by user Evil Dave nearly bankrupted Tom Fulp for good; The United Feature Syndicate kept sending him e-mails which he ignored and mocked, until he found out that he was gonna get hit with serious legal charges. He tried to negotiate by adding a beard on Snarlie and adding a few more changes, but it wasn't enough. Under the risk of having to legally battle them, he settled it out of court with them and removed the movie for good, where it wasn't publicly seen for at least a decade; in 2011, the original version was reuploaded without incident.
- Technology Marches On: Newgrounds staff had to come up with in-house solutions to preserve their massive archive of Flash animations and games, as Adobe ended up dropping support for Flash at the end of 2020 in favor of Adobe Animate.
- The Wiki Rule: The Wikigrounds Newgrounds Wiki, and another Newgrounds Wiki.
Trivia / Newgrounds