WHEN LUE MORGAN DOUTHIT walked onto the grounds of the Oregon Shakespeare Festival (OSF) in Ashland to take a job with the literary/dramaturgy department, she knew this was it. This was the place she'd finally get to produce Lorraine Hansberry's last play, The Sign in Sidney Brustein's Window.

But she'd have to wait a while for that passion to play out onstage—20 years, to be exact.

She had to wait for the festival to hire Bill Rauch as artistic director ("the mensch of all mensches," she says), and she had to wait for Rauch to stage his own passion play—Medea/Macbeth/Cinderella, in 2012.

She had to wait until the festival's head of marketing finally said he thought it was time to do the play that Douthit had been pitching, again and again, to the gathering where about 50 people meet to plan OSF seasons.

Douthit, now OSF's director of literary development, couldn't quite believe it. "It had been such a long battle," she says, "that I made my assistant call me up. 'Did he actually say the words?'"

Yes. The play—a serious, thinky drama—opened in February at the Bowmer, the festival's large indoor theater, alongside lighter fare like the Marx Brothers' The Cocoanuts and Shakespeare's The Tempest. In the smaller Thomas Theatre, a streamlined The Comedy of Errors, set in 1920s Harlem, completes the opening four plays.

The Sign in Sidney Brustein's Window (or, as the festival calls it, Sign) is set in 1964 in Greenwich Village, in the apartment of a man reviewers describe as "an ineffectual Jewish intellectual," and his wife. Their marriage is on the rocks, he's not happy—and politics are starting to shape each character's personal choices.

During the past few years, OSF has seemed almost obsessed with the 1960s, in part because so many of the playwrights making new work for the fest's American Revolutions cycle grew up with that decade as their biggest cultural touchstone. But Douthit says Sign, which was produced on Broadway the same year in which it's set, has different concerns than contemporary plays about that time period.

Where Robert Schenkkan's award-winning 2012 play All the Way was about Lyndon Baines Johnson and Martin Luther King Jr., Lorraine Hansberry—who died in her early 30s of pancreatic cancer—was considering the personal effects of post-WWII philosophy, along with the country's shifting attitudes toward race and gender.

You probably know Hansberry's work from reading or seeing A Raisin in the Sun, her 1959 play about a black family living in Chicago. Sign is different—it's about ideas floating around in Greenwich Village.

In the 1960s, the Manhattan neighborhood "was still a village. It had a community aspect to it," Douthit says. Astute observer Hansberry, who was immersed in the intellectual ferment of the day in coffeehouses, folk music clubs, and living rooms, "captures in a compressed way the ideas that were flowing around."

That means the play's influenced by a philosophy that had a pervasive effect on the post-war generation: existentialism. But lest you worry that Sign is like snoozing through a French philosophy class, Douthit promises that Hansberry also "captures the emotional, the personal behind existentialism."

Indeed, Hansberry's dialogue about civil rights and (straight) marriage dynamics will be "shockingly contemporary," Douthit says.

When Sign ends midsummer, the next play at the Bowmer is precisely chronological—Schenkkan's new play, The Great Society, which picks up after the events of All the Way, and coincidentally just after the events in Sign.

Hansberry never lived to see what happened in LBJ's Great Society. Sign ended its short original run on the night of her death. (Nina Simone wrote to "To Be Young, Gifted, and Black" in tribute to her dead friend.) But Douthit has some thoughts about Sign on its 50th anniversary: "I hope it's a clarion call about what it takes to have a successful democracy—a conversation, and a willingness to listen to people. It's going to be awesome."

Quick Reviews of Oregon Shakespeare Festival's Four Opening Plays

Shows run through November 2, except for Sign, which ends July 3. Details at osfashland.org.

The Tempest—This play about magic, forgiveness, and power features a surprisingly low-key central sorcerer (Prospero, played by Denis Arndt) and a disturbingly debased slave (Caliban, played by Wayne T. Carr). The gorgeous, minimal set and lighting, along with a strong Ariel (Kate Hurster), give it some energy, but not enough.

The Sign in Sidney Brustein's Window—The last play Lorraine Hansberry (A Raisin in the Sun) wrote before she died in 1965, Sign is more prescient about the 1960s than Hansberry could have ever known. This production teems with splendid performances from actors committed to a play that mixes chewy ideas with intense emotions, like love, lust, betrayal, and a fight to make good choices in a world that rewards bad behavior.

The Cocoanuts—This goofball, slapstick Marx Brothers musical was adapted by OSF comedic star Mark Bedard, who played Groucho in 2012's Animal Crackers and reprises his role here. Awards to the stagehands for getting the huge, bright set on and off the stage. The songs are fine, the prewritten jokes aren't that funny—but Bedard, John Tufts as Chico, and Brent Hinkley as Harpo make audience interaction into different comedic gold every performance.

The Comedy of Errors—This early play, in which Shakespeare doubles down on twin jokes and farce, stands out as the gem of the opening productions this year. From fabulous video projections that bring 1920s Harlem to life to colorfully perfect costumes to brilliant acting by pretty much the entire cast, Comedy (in the small Thomas Theatre) brings both laughs and poignancy as long-parted family members find their way back to each other.