Actor, famous for “Office Space” scene, takes on real estate in Sarasota County

Actor and Realtor for Coldwell Banker, Gregg Pitts, near his downtown Venice office. Pitts is best known for his role in the cult movie "Office Space." (Photo by Matt Houston )

Greg Pitts, actor and realtor for Coldwell Banker, near his downtown Venice office. Pitts is best known for his role in the cult movie "Office Space." (Photo by Matt Houston )

VENICE — In Hollywood, he may forever be known as the “O-face” guy.

But now, Greg Pitts is trying to make a new name for himself in Southwest Florida real estate.

Ron Livingston and Greg Pitts, right, in Pitts' famous "O-face" scene from the 1999 cult comedy "Office Space."

Ron Livingston and Greg Pitts, right, in Pitts' famous "O-face" scene from the 1999 cult comedy "Office Space."

The actor — famous for an unforgettable scene in the cult comedy “Office Space” — recently moved back to his hometown of Venice to follow in the footsteps of his family and begin a second career as a Realtor.

From the conference center in his brokerage — just a block from the beach, with views of the shops and cafes that line Venice Avenue — Pitts said it was time for a change. Real estate just felt right.

“I knew I always wanted to come back, at a bare minimum to buy a second home here,” Pitts said, wearing a Coldwell Banker name tag on his white business shirt. “For me, acting became a little less satisfying as a career because I didn’t feel engaged enough.”

Pitts was born at Sarasota Memorial Hospital in 1970 — growing up in the Sorrento Shores community that his grandfather developed. His father runs a real estate business — which his brother later joined — in Osprey.

Pitts remembers answering the phones, riding tractors to clear land at Sorrento Shores and hand painting every single fire hydrant in the subdivision to meet a new safety code — twice because he had the color wrong.

He had an early knack for real estate, but a passion for the stage.

His father was involved with community theater, prompting Pitts to take his first acting class while a senior at Venice High School.

But it was while Pitts was dozing off in college business lectures that he realized his hobby was instead a calling. He swapped suits and briefcases for dreams of the stage and cameras.

After graduating from the University of South Florida with a degree in theater in 1992, he moved to Hollywood with $1,100.

He did work for a traveling Wild West show, a gig that remains one of his favorites. He performed with the Groundlings, a comedy troupe whose alumni includes Will Ferrell, Kathy Griffin and Kristen Wiig.

Pitts also worked at a Blockbuster video store, at the House of Blues and as a production assistant, sometimes changing clothes in his car between shifts at all three jobs in a single day.

In his scarce free time, Pitts would scour production magazines — sending headshots and a noticeably empty résumé to every opening he could find.


With gigs few and far between, Pitts and 10 of his fellow actors wrote their own screenplay for a small Hollywood venue called Theatre Theatre that’s now home to a car rental company.

They hoped the sketch comedy effort would separate them from the thousands of aspiring actors jostling for relevance in Los Angeles.

But the newspaper would not review the show until they booked a theater for four consecutive weeks. So the group pooled their money. Pitts even walked Hollywood Boulevard, soliciting buyers for advertisements in the program.

The show sold out for 18 straight weeks in 1997.

Success split the band, and led to Pitts’ first TV appearance: a role alongside stand-up comedian Damon Wayans in the series “Damon.”

It lasted 13 episodes.

But “Office Space” — and the silver screen — was next.

The 1999 movie, written and directed by “Beavis and Butthead” creator Mike Judge, featured actors Jennifer Anniston, Ron Livingston and Gary Cole.

Livingston plays a disgruntled employee at a software engineering firm, who, along with his coworkers, plant a virus in their company’s accounting system to embezzle a fraction of the financials.

Pitts’ character — an obnoxious blond named Drew — had fewer than five minutes of screen time. But the 20-second scene where he shows his fellow coworkers the “O-face” — his purported expression in the moment of orgasm — became one of the most memorable scenes and still lives on in jokes today.

Pitts said that scene was scripted differently. He improvised the “O-face” that made it through the final cut.

“I’m wondering if these people think I’m crazy,” Pitts said with a smile, recalling the moment. “Then everyone laughed, and I knew we had something.”

'Pinball effect'

“Office Space” was a flop in theaters, grossing around $11 million.

But through DVD sales and TV broadcasts throughout the years, it became one of 20th Century Fox’s best-known “second-wind” flicks.

Pitts still gets checks every time his “O-face” airs.

That success ushered in other opportunities for Pitts, with roles on the TV series “Normal, Ohio"; a guest character role on “Grey’s Anatomy,” “Monk” and “Bones"; and film roles in “Coyote Ugly” and “Idiocracy.”

“There’s a pinball effect,” Pitts said. “When you have such a memorable impact, everyone wants you to play that same character in other things because you’re so identifiable. It’s flattering, but it also can be an encumbrance because it forces people to see you in one way.”

Pitts got his own second wind from an advertising campaign by Allstate Insurance, where he can be seen tailgating at football games before disaster strikes his car. There’s one bit where his friends think they spot legendary coach Bobby Bowden, only to have their driver’s side door dislodged by an oncoming motorist.

When Pitts goes out to eat, he still gets the looks: Was it high school? A former job? Where do I know him from? Most quickly figure it out.

“When you’re in a small town like this, you don’t expect the people you’re around to be the guy you saw on TV,” Pitts said. “It becomes a fun talking point.”

Florida return

Pitts moved back to Venice in late 2011 with his girlfriend, another Southwest Florida native, to spend time with his dying mother.

Now 44, he got his real estate license last year, joining Coldwell Banker — the same firm that his father and brother are associated with.

Pitts — who still acts on the side, with a studio built into his house for auditions — says he always knew the housing market would be his likely fallback plan. He recently closed on his first deal as an agent.

He hopes the experiences and connections he gained through Hollywood will help build his name into an industry brand. He plans on using any recognition he has to his advantage.

It worked recently when Pitts pulled up in his pickup to meet new client Sonia Kuster for the first time.

She immediately thought of “Office Space” — one of her favorite movies. Kuster had been referred to Pitts by an associate at Venice Bank.

“I said man, he’s a dead ringer for that guy in ‘Office Space,' ” Kuster recalls thinking. “But I figured it would be really rude if I asked him, and anyway, it couldn’t be.”

The two had almost made it through that entire first showing before Pitts’ background came up.

Even with comedy in his blood, Kuster said Pitts was one of the most professional Realtors she has worked with. The property was bank-owned. Liens and lender issues stalled the process — and heightened frustrations. Pitts still managed to close the deal.

“He just worked really hard and didn’t stand to make much,” she said. “He kept in contact every day no matter what. There were times I wanted to throw in the towel, and he really went all out for me.”

Stacey Licking knew Pitts from their days in high school. The two friends drifted apart, but Licking continued to follow Pitts on the screen. After a class reunion, Licking enlisted Pitts as a Realtor.

“Even if its 10 or 11 p.m., if I see something I like, he responds right away,” Licking said. “Any place, any time, he’s available.”

Presumably, without the “O-face.”

Last modified: February 24, 2014
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