MS Paint Adventures

Jailbreak, the first adventure written by Andrew Hussie, was originally a forum game following an unnamed man as he attempts to escape from a prison cell.[3] The first page of Jailbreak is the only panel of any MS Paint Adventures work actually created using MS Paint; Hussie created the rest of Jailbreak and later webcomics using Photoshop.[16] Jailbreak was written entirely as a forum adventure, and the first suggestion anyone posted was taken, however ridiculous, leading to a rambling and haphazard story line. Jailbreak was only drawn to a vague conclusion, and Hussie considers it unfinished, but wishes to leave it as is. This led to the creation of the MSPA site and the closed format of later adventures.[17] In 2011, a short official ending was added to Jailbreak as a callback during a notably lengthy Homestuck hiatus.

The second adventure, Bard Quest, was an experiment in creating multiple, branching paths rather than a single linear storyline. In Bard Quest, Hussie provided choices as hyperlinks in a choose-your-own-adventure format.[16] It was the first adventure to be hosted on its own website, but was ultimately left unfinished due to the difficulty Hussie faced in maintaining the complex web of branching storylines.[17] Bard Quest was updated from June 12 to July 6, 2007, after which the site was left on hiatus.[18]

A parody of interactive fiction games and the film noir genre, Problem Sleuth began by presenting three detectives who are attempting to escape from their respective offices, though the story quickly turned into a pastiche of video games and science fiction.[5] Problem Sleuth ran from March 10, 2008, to April 7, 2009.[19] Unlike its predecessors, it received a proper ending, becoming the first complete adventure. It is the second-longest comic on the website so far, after Homestuck, with 1,674 pages.

Homestuck is the longest adventure hosted on MS Paint Adventures with over 8,000 pages and over 800,000 words.[20] It ran from April 13, 2009, to October 25, 2016, and followed four teenagers as they play a reality-altering video game that brings about the end of the world. They must work with an alien species from another universe to create their own universe and essentially become its "owners". Homestuck's basic premise is inspired by games like The Sims, Spore and EarthBound.[2] As in Problem Sleuth, the adventure is characterised by time travel, mystery, a complex fictional universe, and frequent references to pop culture and previous adventures. Changes from previous stories include an emphasis on contemporary society, such as online gaming and Internet culture, which contrasts with the historical settings of Bard Quest and Problem Sleuth.[5] Additionally, this adventure introduced complex Flash animations and games, many making use of music and assets contributed by other artists.[21] This represented a step-up from previous adventures which exclusively used GIF images for animation. Ten major soundtrack albums have been released under the comic's own record label, What Pumpkin, in addition to fourteen side albums.[3][22]

Homestuck has a large following and fandom. Homestuck has been compared to James Joyce's Ulysses in relation to the webcomic's complexity and how the task of finishing it is an example of effort justification.[23][24] Homestuck's Adventure Game Kickstarter reached approximately $2,485,506 of a pledged $700,000 by the ending of the fund, and had 24,346 backers. The video game was expected to be released some time in early to mid 2015, but was delayed to January 2016 and then again to January 2017 until September 14, 2017, when Hiveswap was released. Hussie also stated that he will make an epilogue for Homestuck with Viz Media's help.

Sweet Bro and Hella Jeff is a spin-off of Homestuck. Within Homestuck, the comic Sweet Bro and Hella Jeff is written by the character Dave Strider from Homestuck, and several actual comics were produced by Hussie. It is presented in a different format than the other adventures, formatted more similarly to that of a traditional comic, having multiple panels per page.

Other works have been sequels of MS Paint Adventure stories, but never hosted on that website. The Homestuck Epilogues is a partially canon continuation of Homestuck that ran from April 13 to April 20, 2019. This also is formatted differently from the other adventures, as there are no pictures. There are two different plotlines, a "more canon" one represented by meat, and a "less canonical" one, represented by candy. Homestuck^2: Beyond Canon is Hussie's second most recent work. It was launched on October 25, 2019, and continues the plot of Homestuck and its epilogues. The new webcomic is a collaboration between What Pumpkin and Snake Solution Studios LLP. It started with a new writing team led by Kate Mitchell and Andrew Hussie, who both later resigned from the writing team and the comic was put on hold indefinitely on December 25, 2020. The comic is now being written privately and will be published all at once at an as of yet undetermined date.[25]