Jimmy Kimmel made a guest appearance on HBO's satirical series "Life, Larry and the Pursuit of Unhappiness: An Almost History of America," where he joined host Larry David in criticizing former President Donald Trump. The show, executive produced by Barack and Michelle Obama, featured Kimmel in colonial attire, delivering lines that implicitly targeted Trump without naming him.

In one scene, David's character, dressed as George Washington, questioned the potential for a "narcissistic p---- who doesn’t follow the Constitution" to be in office. Kimmel's character responded skeptically to the idea that a president would react strongly to criticism, referencing a previous joke he made about first lady Melania Trump.

Kimmel previously faced backlash for a joke describing Melania Trump as an "expectant widow." He later clarified that the remark was intended to comment on the age difference between the Trumps. Trump himself has publicly called for ABC to fire Kimmel, citing dissatisfaction with his show's ratings.

The HBO series also featured a posthumous appearance by the late director Rob Reiner, who played George Washington. The character discussed the importance of a peaceful transfer of power and proposed an amendment to limit presidential authority.

Kimmel has increasingly incorporated political commentary into his late-night show in recent years. He faced a brief suspension from Disney in the past over controversial remarks, which he later stated were not intended to make light of a specific death.