After Justin Timberlake opened the award ceremony with a performance of his hit song "Can't Stop the Feeling," Kimmel took the stage and encouraged the members of NSYNC to allow Timberlake back into the group.
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Kimmel was just getting warmed up as he prepared to rip into Damon. The host of "Jimmy Kimmel Live!" appeared to be burying the hatchet with his longtime foe, but immediately turned the tables.
"I've known Matt for a longtime. I've known Matt for so long that when I first met Matt, I was the fat one," Kimmel said.
After the crowd roared with laughter at the expense of Damon, who is up for an Oscar for his work on "Manchester by the Sea," Kimmel turned his attention to Trump.
"Maybe this is not a popular thing to say, but I want to say thank you to President Trump," Kimmel said. "Remember last year when it seemed the Oscars were racists?"
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Kimmel took more shots at Trump while addressing Meryl Streep, who received her 20th Oscar nomination.
"(She) has stood the test of time due to her very uninspiring and overrated performances," Kimmel quipped, referencing a tweet Trump sent in January following a speech from the actress at the Golden Globes.
White House Press Secretary Sean Spicer said last week that Trump would not be watching the Oscars for "a Meryl Streep kind of moment."
Streep received a standing ovation, leading Kimmel to ask if she was wearing a dress from the Ivanka Trump collection.
Kimmel then projected that Trump would tweet about the Oscars in the morning "during his bowel movement."