In the summer of 1988, a fateful car drive landed Bill Rauch in the southern Oregon town of Ashland for the very first time. By day he was smitten with the natural beauty of the area, by night it was the Shakespeare. But it would be another 19 years until the gorgeous mountains became his permanent backyard and he would find himself at the helm of the largest resident theater company in the nation — the Tony Award-winning Oregon Shakespeare Festival.

Known for taking risks (“Hamlet” does hip-hop? More on that later.), the 1984 Harvard grad spent 20 years mixing things up on stage as co-founder of the experimental Los Angeles-based Cornerstone Theater. He also directed dozens of plays and taught theater at UCLA, USC and other universities before finally making his way back to Oregon.

This February, Rauch kicks off his fourth season as Oregon Shakespeare Festival’s Artistic Director — and what a season it will be. The 11-play repertoire includes four Shakespeare pieces, a literary classic (“To Kill a Mockingbird”), a modern comic tragedy (Tracy Letts’ “August: Osage County”) — even a world premiere (“Ghost Light” by Tony Taccone). And, for the first time ever, OSF will produce a large-scale classic musical (“The Pirates of Penzance”), featuring a 14-piece orchestra, on its outdoor Elizabethan stage.

“People who don’t know OSF think of it as a short season,” says Rauch. “They don’t realize the length.” This year alone, Rauch and his 500-person team will sell more than 400,000 tickets and put on a staggering 822 performances from February to November. And Rauch is in charge of it all — not to mention, he’s simultaneously securing plays, and picking directors and actors for the 2012 and 2013 seasons.

“People come to OSF for a variety of experiences,” says Rauch. “It’s my job to make a kaleidoscope of colors as bright and varied as possible.” And he’s doing so with gutsy gusto.

In his four years at the top, Rauch has radically increased the amount of new work commissioned by OSF, now in its 76th season; launched a 10-year project to create 37 plays about American history; and created the Black Swan Lab, charged with developing new works for the stage. Rauch is especially talented at putting new spins on old classics; last year’s audience won’t soon forget how he brought “Hamlet” into the 21st century with modern getups and a hip-hop scene at the castle.

So, what has the hardest working person in theater aflutter this season? Rauch is directing “Measure for Measure,” his favorite Shakespeare play. “It’s funny, dark, and hard to categorize but it looks at the collision between politics and morality,” he says. “It’s a brilliant play with a strong cast and it’s going to be a knock out.”