This Hollywood Actor, 45, Sent Jean Smart, 73, a ‘Cheeky’ Autographed Pic originally appeared on Parade.
Jean Smart became unsuspecting pen pals with a younger Hollywood gentleman, which blossomed into a “cheeky” friendship.
The Frasier actress, 73, stopped by Late Night with Seth Meyers on Thursday. August 7, and revealed her silly bond with John Krasinski.
“We have the same vocal coach. So, we would trade messages,” Jean explained how she first met The Office star, 45. “I’d say, ‘Oh, I’m such a fan.’ And then we’d trade each other inspirational messages to put in our dressing room.”
Despite not yet meeting in person, Jean and John’s quote exchange turned into transfers of wine.
“And then he sends me this …” Jean said, pointing to a photo in Seth’s hand.
John sent Jean an autographed picture of himself as Jim Halpert in The Office, with the message, “To Jean – you seem like a great kid. Keep reaching for the stars!”
“I believe that is the definition of cheeky,” the Call Me Izzy Broadway star joked.
Meanwhile, Seth, 51, thought it was funny that John chose to pick a character from his “Office era” over Jack Ryan.
That said, the moment Jane and John finally met may have been even funnier. The Designing Women star shared that she scored tickets for her and her assistant, Molly, to attend John’s opening show of Angry Allen, including an invitation to the opening night party.
“She got to meet him. She’s very petite and he’s very tall,” the Emmy award-winning actress explained. “And she said, ‘Oh, Jean, I was so embarrassed. I was so atwitter when I met him. He’s so cute and he’s so tall.’”
John’s good looks even got Jean to forget her name as she introduced herself to him, “I said, ‘Hi, I’m Molly. Jean Smart is my assistant!’”
According to the Hacks actress, John looked at her assistant and nonchalantly replied, “Cool.”
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This Hollywood Actor, 45, Sent Jean Smart, 73, a ‘Cheeky’ Autographed Pic first appeared on Parade on Aug 8, 2025
This story was originally reported by Parade on Aug 8, 2025, where it first appeared.
