When your movie is nominated for best motion picture of the year at the Academy Awards, you tend to score some pretty good seats at the ceremony. In 2011, film producer and first-time Oscar nominee Gary Gilbert, ’86, found himself in the fifth row, on the aisle, and directly behind actor Mark Wahlberg. Gilbert’s movie The Kids Are All Right, starring best-actress nominee Annette Bening, was up for four Oscars. The film had picked up two Golden Globes already, including Best Motion Picture—Musical or Comedy.

Actress Annette Bening and film producer Gary Gilbert, ’86, celebrate their Golden Globe victories for The Kids Are All Right in 2011. (Image courtesy of Gary Gilbert.)

As the producer straightened his shiny new tux and scanned the crowd, he saw Bening’s competition, Natalie Portman, who would win best actress for Black Swan. She’d co-starred in Gilbert’s first movie, Garden State, back in 2004.

“Growing up, people would tell me a career in Hollywood was a pipe dream,” says Gilbert, 47. “But I can tell you, it’s not.”

Getting down to business

Gilbert, or “Globe-bert” as older brother Dan—majority owner of the Cleveland Cavaliers—likes to call him, recently completed his ninth film, Quad, starring Jeff Daniels. The crew shot on location in Michigan as Gilbert is a strong advocate for production in his (and Daniels’) home state. After all, it was the old Berkley Theater in suburban Detroit where Gilbert’s passion for movies was born.

“I always loved going to the movies,” he says, citing such favorites as Butch Cassidy and the Sundance Kid and Papillon. Gilbert’s tone turns wistful as he recalls childhood memories at the drive-in with his late father, Sam, who ran the popular Detroit restaurant Saksey’s.

“He loved to take Dan and me to the drive-in where we’d see films like Magnum Force and Death Wish,” Gilbert says, “and our mother would drop us off at the Berkley matinee on Saturday afternoons.”

In high school at Southfield-Lathrup, Gilbert got his first taste of show business playing drums in the band Joint Session with childhood pal Brian Kerwin, ’86. Initially, he joined older brother Dan at Michigan State, but ultimately enrolled in the undergraduate program at Michigan’s Stephen M. Ross School of Business.

“The basic economics of what I know today came from the classes I took at Ross,” Gilbert says. “Some of my closest friends today were my roommates back in Ann Arbor. It was an incredible time of personal development.”

It was an incredible time of professional development, as well. In the summer of 1985, Gary and Dan evolved from brothers into business partners. As Gary prepared for senior year, Dan founded the mortgage-lending business Rock Financial with $5,000. Gary bought a large share in the venture—and the rest, as they say, is history.

“It was two of us in a 10-by-10-foot office schmoozing realtors and selling mortgages,” Gilbert says.

They did it very well. In 1998, Rock Financial went public, and 18 months later, the brothers sold the firm to software giant Intuit Inc. for $532 million. Today it is known as Quicken Loans.

After the deal closed, Gilbert faced a life-changing choice: He could continue working for his brother, or venture out and create something on his own. “If I stayed, I felt I would forever be in Dan’s shadow,” he says. “I remember thinking, ‘There’s only so long you can work for your older brother.'”

So Gilbert moved to New York to figure out his next move. He looked into funding Internet startups, but he found the prospect less than inspiring.

“I asked myself, ‘What do I love?'” he says. “I love the movies.”

Globe-bert strikes gold

In 2000 Gilbert set his sights on Los Angeles. For the next five years, he would average one week a month there, setting up shop at the Four Seasons Hotel in Beverly Hills. He started Camelot Pictures with a partner, learning the finance and production side of the movie business. But he remained unfulfilled. Working as a producer-for-hire entailed countless meetings with studio executives in the never-ending quest to attach oneself to as many projects as possible in the hope one would hit big.

“I wanted to make a movie, be on a set every day, and finance something myself,” Gilbert says.

As he began searching for an independent film to finance, Gilbert discovered an intriguing script by a young actor named Zach Braff whose star was on the rise. Braff was coming off his first season in the quirky ABC hospital comedy “Scrubs.” Braff not only wrote the screenplay for Garden State; he also wanted to star and direct.

“When everyone in Hollywood with a phone and a desk passed on Garden State,” Braff says, “Gary was the only one who said yes. He was willing to gamble on me with my very first chance in the director’s chair.”

That gamble paid off, both personally and professionally. Gilbert financed Garden State for $2.5 million and co-produced with Jersey Films. He spent every day on the set, learning the business under Jersey Films’ Pamela Abdy, a former studio executive at Paramount.

“It was like going to film school,” he says.

Watching the garden grow

Garden State was a breakout hit at the 2004 Sundance Film Festival. Fox Searchlight and Miramax bought the movie with a $5 million advance and a piece of the back end. The picture would go on to earn $27 million at the domestic box office. It also won the prestigious Independent Spirit Award for Best First Feature.

For Gilbert, there was no turning back. He was now a moviemaker.

“It was special,” Gilbert says of the Garden State experience. “We were the largest sale at Sundance that year and we did it again at Sundance in 2010 with The Kids Are All Right.”

After spending 14 years in the very predictable mortgage business, Gilbert says he thrives amid the inherent chaos of filmmaking. “Your seven thousandth mortgage is the same as the first,” he says. “With movies, you’re reinventing the wheel every time and you don’t know the outcome—how the audience receives it when they see the finished product.”

Even if the movie is a box-office bust, you still get to work with some pretty cool people, he notes. Since forming his latest company, Gilbert Films, in 2009, the former mortgage lender has produced comedies and dramas starring Matt Damon, Anna Paquin, Mark Ruffalo, Julianne Moore, and Kim Cattrall, among others.

But the real fun came during the 2011 awards season when Gilbert received that first Oscar nomination for producing The Kids Are All Right. The quirky love story follows a lesbian couple portrayed by Bening and Moore. They each have children by the same sperm donor, Ruffalo, who wreaks emotional havoc when he re-enters their lives.

During the red-carpet bonanza of back-to-back awards shows, Gilbert got to know Bening’s husband, Warren Beatty, the award-winning actor/director/writer/producer behind Heaven Can Wait, one of Gilbert’s all-time favorite films.

“We struck up a friendship,” he says. “He loves to give advice and he has great stories.”

Lights, camera, action

Now that he’s racked up some impressive experience and accolades for producing, Gilbert is entertaining the idea of directing.

“I just love the creative part of filmmaking,” he says. “I have a heck of a lot more fun working with a film editor than I do taking meetings and making conference calls.”

That comes as no surprise to brother Dan, who always encouraged his younger sibling to pursue his passion.

“He’s doing it,” Dan says. “If you have a dream, make it happen. Gary’s proof of that.”

Adds Braff: “Gary has a business mind, but he approaches producing first and foremost from the point of view of a lover of movies.”

It’s a love Gilbert is anxious to share. When he meets aspiring filmmakers and actors, he offers no cautionary tales. He flat-out tells people to go for it.

“You can make it, even by default, if you put in the time,” Gilbert says. “You need talent, heart, street smarts, and a willingness to put in the years of work. If you have those four qualities, it’s almost hard not to make it.”