Stephen Colbert Mocks Trump’s Iran Strategy with Sharp Humor on 'The Late Show'

Stephen Colbert, host of The Late Show, delivered a sharp critique of President Donald Trump’s erratic approach to the Iran conflict during Monday night’s episode, coinciding with the 4/20 holiday.

Colbert opened his segment by addressing the recent back-and-forth over the Strait of Hormuz, where Iran reopened and then reclosed the strategic waterway in response to the U.S. maintaining its military blockade.

"I believe the real Strait of Hormuz was the friends we made along the way. And I’m being told we made no friends," Colbert joked, referencing Trump’s prior claim that Iran had promised never to close the Strait again. "And they never did … until the next day when Iran closed the Strait of Hormuz again. Oh, so close."

He also mocked Trump for prematurely celebrating the conflict’s resolution, advising,

"Don’t jinx it! You can’t talk like that until the situation is fully resolved. He sounds like a cop in an ’80s movie, one day from retirement, pointing at a picture on a desk saying, ‘Yep, that’s my daughter, Denise. In the summer, I’m gonna walk my little girl down the aisle.’"

Colbert further lampooned Trump’s weekend posts on Truth Social, where the president shared a series of videos described by Colbert as "deranged" self-praise. One video featured an AI narrator urging Trump’s supporters to "let him cook."

"Always reassuring when you hear a world leader use Gen Z slang," Colbert remarked. "I’m reminded of the immortal words of Mahatma Gandhi: ‘You must be the change you wish to see in the world. Wow, fam, I ate with that.’"

The segment aired on April 20, 2020, during Colbert’s regular Monday night broadcast of The Late Show.