Jimmy Kimmel Teams up With Obama for Trump Satire on HBO

WHO:

NY Post - Jimmy Kimmel, Barack Obama, Michelle Obama, Rob Reiner, Larry David, Melania Trump

Fox News - Jimmy Kimmel, President Trump, Rob Reiner, Larry David, Melania Trump

WHAT:

NY Post - Kimmel made a cameo appearance on Larry David’s HBO program to mock Trump.

Fox News - Kimmel doubled down on his controversial "expectant widow" joke about Melania Trump.

Fox News - Rob Reiner made a posthumous appearance as George Washington in the HBO satire series.

Fox News - The HBO satire series lampooned Trump without mentioning his name.

Fox News - Kimmel's character questioned the idea that a president would retaliate against critics, saying, "Come on, that could never happen."

WHERE:

NY Post - HBO

Fox News - HBO’s "Life, Larry and the Pursuit of Unhappiness: An Almost History of America"

WHEN:

Fox News - Kimmel appeared on the show on July 3.

WHY:

Fox News - Kimmel has ramped up his liberal political commentary in recent years, particularly targeting Trump.

HOW:

Fox News - Kimmel's character in the show mocked the idea of a president attacking the free press to silence criticism.

(UPDATED July 6, 2026 23:23 UTC)

Jimmy Kimmel made a cameo appearance on HBO's "Life, Larry and the Pursuit of Unhappiness: An Almost History of America," where he mocked President Trump and doubled down on his controversial "expectant widow" joke about Melania Trump. In the episode, Kimmel's character questioned the notion that a president would retaliate against critics, humorously suggesting that such behavior could never happen. Meanwhile, Rob Reiner made a posthumous appearance as George Washington, as the show lampooned Trump without directly mentioning his name.