Guard Dog (2004) was also nominated for the Academy Award for Best Animated Short Film. In 2005, Plympton animated a music video for
Kanye West's "
Heard 'Em Say" and the following year, he created the music video for
"Weird Al" Yankovic's "
Don't Download This Song". Plympton contributed animation to the 2006
History Channel series
10 Days That Unexpectedly Changed America, to illustrate the events of
Shays' Rebellion. Together with other independent New York City animators, he has released two
DVDs of
animated shorts, both titled
Avoid Eye Contact. Plympton's 2008 80-minute feature,
Idiots and Angels presented by
Terry Gilliam, had no dialogue. The film premiered at the
Tribeca Film Festival on 26 April 2008, In 2011, Alexia Anastasio completed a documentary on Plympton's life,
Adventures in Plymptoons!, released in September 2012
direct-to-DVD and on
video-on-demand. In 2011, Plympton collaborated with child film critic Perry Chen on
Ingrid Pitt: Beyond the Forest, a 2011 short animated film directed by
Kevin Sean Michaels, about actress and
Holocaust survivor
Ingrid Pitt. Plympton has done extensive guest animation work for
The Simpsons, producing eight opening
couch gags for the show between 2012 and 2022, as well as the menus and packaging for the Season 19 DVD. Plympton directed the segment "On Eating and Drinking" in the 2014 animated film
The Prophet, adapted from
Kahlil Gibran's book
The Prophet. In 2018, Plympton created a series of videos for
The New York Times called “Trump Bites”. One of the series,
Trump and Putin: A Love Story, depicts Trump and Putin kissing half-naked. Critics said the video implied that gay relationships were inherently comical and immoral. In 2020, Plympton released a
Kickstarter for a new animated comedy western,
Slide. The funding was successful, raising $60,000 from 400 backers. The film premiered at the 2023
Annecy International Animation Film Festival and was shown at several other film festivals through 2023 and 2024. In November 2025,
Slide was released to 80 screens in France with the title
Duel à Monte-Carlo del Norte. In August 2025, Plympton announced a new animated short entitled
Whale 52 - Suite for Man, Boy, and Whale which had its New York premiere in September at the
IFC Center in New York City as part of a multi-day Plympton retrospective produced by
"Weird Al" Yankovic, where another Plympton animated short,
Duckville, also had its NYC premiere.
Whale 52 played at the 2025
Woodstock Film Festival and was one of 113 Oscar-qualified animated shorts. Although it was not nominated for an Academy Award, in February 2026
Whale 52 screened at the
Berlin Film Festival and received the Crystal Bear award for Best Short Film. ==Technique==