Jim O'Heir says William Shatner treated him with 'disgust' during “Boston Legal” guest spot where he was in drag

Shatner says he was acting.

Jim O'Heir is best known for playing Jerry Gergich, the inoffensive Indiana office worker everyone loved to hate on Parks and Recreation. It was always clear that O'Heir's Parks colleagues really did adore him under all the faux contempt, but when guesting on Boston Legal opposite William Shatner, O'Heir second-guessed the star's apparent animus.

On the 2004 Boston Legal episode "Loose Lips," O'Heir played Gil Furnald, a man who is "fired from his post as Santa at a department store after it’s revealed that he enjoys wearing women’s clothing." As O'Heir explains in his new book Welcome to Pawnee: Stories of Friendship, Waffles, and Parks and Recreation, "In some parts of the country today, this might not be seen as a progressive, boundary-pushing plot, but in 2004 it wasn’t far off."

O'Heir continued that series star "William Shatner himself wasn’t okay with this. Nor was his character. In one scene, when Gil Furnald tells Shatner’s Denny Crane his reasoning behind dressing up as a woman ('It’s not a sexual turn-on. It... well... it just feels right sometimes'), Denny Crane responds, 'So, basically you’re a sicko?'"

O'Heir believes that "the writers of this episode were attempting to pry into the expectations that society places on those who don’t adhere to 'normal' ways, whatever that word means, but off-screen, it appeared that William Shatner might have been falling victim to the very thing the show’s writers were exposing."

"Whenever my character wore a dress or earrings, Shatner appeared to be aloof, sometimes even cold, to me," he explained. "He kept scanning me up and down, his floppy smile transformed. Was it disgust? At one point between takes, he said to [James Spader], 'Thank God, this is yours,' seemingly glad that Spader’s character, and not his, would be legally representing Gil in this episode. I don’t know if Shatner was joking, or maybe he’s a Method actor, or maybe I was just overly sensitive. Whatever it was, it definitely made me uncomfortable."

When reached by Entertainment Weekly for comment, Shatner remarked, "I have no idea why this wonderful actor would think that I, Shatner, would be the same character as the fictional one I was playing. There’s a real difference. I hope he knows that."

Related: Jim O'Heir details infamous 'makeout sesh' with Parks and Rec costar Aubrey Plaza in book excerpt: 'I just agreed to WHAT?!'

The David E. Kelley-created legal procedural that premiered in 2004 was a spinoff of the popular series The Practice. It was James Spader's Practice character that Boston Legal was formed around, but Shatner's eccentric Denny Crane, the cocksure conservative who proudly stomps around, referring to himself in third person, often stole the show.

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Crane shared many of Shatner's own idiosyncrasies — the slightly out-of-touch joviality, the blustering self-importance. But the politics? Shatner has long refused to put his finger on the scale, only weighing in, in fact, when people try to assign politics to his characters, as Texas senator Ted Cruz attempted in 2015.

Other actors who've worked with Shatner have opened up about their less-than-positive experience of him in the past. Most notably George Takei, who starred as Hikaru Sulu opposite Shatner's James T. Kirk on several Star Trek series and films over the years. Takei called Shatner a "cantankerous old man" in 2022, remembering him as "self-involved. He enjoyed being the center of attention. He wanted everyone to kowtow to him."

Related: Watch William Shatner get a second chance at Captain Kirk's Star Trek Generations death scene

Showing up for a day of filming with a cast and crew that are already a well-established family is intimidating enough, but that day on the Boston Legal set, O'Heir felt extra vulnerable, given that he had to "show up to set on my first day in a dress and high heels in front of the cast and crew."

O'Heir continued appearing in guest spots on series like Desperate Housewives, Monk, and Curb Your Enthusiasm before landing the role of Jerry on Parks in 2009. He and costar Retta would work five seasons on that show before being promoted from recurring characters to main cast.