For a fairly small town, Key West has some seriously impressive theater options and the Waterfront Playhouse is one of the best. Dubbed “Best Professional Theater in Florida” by Florida Monthly Magazine, the Waterfront Playhouse, a not-for-profit professional theater, has been at the forefront of bringing cutting-edge theater straight from Broadway to Monroe County. This season marks the theater’s 77th year and the Waterfront shows no sign of stopping its award-winning performances anytime soon.

The Waterfront Playhouse began in 1939 when the Key West Players, the original producers, formed a troupe including locals and Navy personnel to put on theatrical productions wherever they could find space to perform. This often included unconventional locations, such as the U.S.S. Gilmore, which was docked in Key West after World War II. The Key West Players moved into their current location on the historic Mallory Square in 1960, into a building that used to be an ice warehouse in the 1880s.

Danny Weathers, second from right, appearing in “A Chorus Line.”

Most people who work with and at the Waterfront Playhouse would say that Danny Weathers, the managing artistic director, is the driving force of the theater. Mr. Weathers joined the Waterfront Playhouse in 2003 and has held just about every role one can have in a theater. He has directed 31 productions in his 13 years at the Waterfront Playhouse, as well as multiple concerts and special theater events. In addition, Mr. Weathers is an immensely talented actor. Before he graced the Waterfront stage, Mr. Weathers performed in the cast of “A Chorus Line” on Broadway as Gregory Gardner, a role he played for over four years.

He has also been in a number of Off- Broadway productions, the film version of “Annie,” and in concerts with the Rodgers and Hammerstein Organization at Symphony Space in New York Cityand at the Smithsonian in Washington, D.C. At the Waterfront, Mr. Weathers has acted in “The Drowsy Chaperone,” “Lend Me a Tenor” and “Little Shop of Horrors.” The Waterfront Playhouse owes its success in large part to Mr. Weathers’ creative vision and vast production experience and talent.

Danny Weathers, managing artistic director of the Waterfront Playhouse. 

The Waterfront Playhouse begins every season with a grand kickoff concert that features local vocal talents and typically adheres to a particular theme, often highlighting a musical artist or cultural event such as the Academy Awards. This year, the concert is this weekend on the evenings of Nov. 18 and 19 and the theme is “What the World Needs Now: A Tribute to Burt Bacharach.” An accomplished group of Key West’s best singers will sing the timeless hits of the six-time Grammy Award winner and three-time Academy Award winner. Opening night tickets cost $75 and include a post-show catered party to celebrate the official start of the season. Tickets for the second night are $50.

Mr. Weathers might say that this is one of the most ambitious seasons in the storied history of the Waterfront Playhouse. The first production on the Waterfront’s calendar is “It’s Only a Play,” by Terrence McNally. The comedy takes place on opening night of “The Golden Egg” at a party hosted by Peter Austin, the playwright. With his career on the line, the high-anxiety playwright shares his big night with his television star best friend, the doped-up star of the show, his novice producer, his director, a brutal drama critic and a coat-check attendant on his very first night in Manhattan. The original cast on Broadway included Nathan Lane, Matthew Broderick and Megan Mullally, and the show was labeled “wickedly funny” and “uproarious.” “It’s Only a Play” will run from Dec. 13 to Jan. 7 every Tuesday through Saturday, with the exceptions of both Christmas Eve and New Year’s Eve.

The next show on the schedule is “The Trip to Bountiful,” by Horton Foote. The protagonist Carrie Watts is an elderly widow trapped in a tiny Houston apartment with her overprotective son and daughter-in-law. Carrie dreams of returning to her hometown of Bountiful one last time before she dies, but her son will not let her travel alone. And so, with her pension check in hand, she escapes from the apartment and boards a bus to Bountiful. Filled with both humorous and tender moments, this play focuses on the universal connection we all have to “home.” “The Trip to Bountiful” stars the talented Joy Hawkins and will run from Jan. 24 through Feb. 11 every Tuesday through Saturday.

After the daunting yet successful undertaking that was “The Producers” last season, it seemed impossible for the Waterfront Playhouse to top its musical game but this season brings yet another ambitious musical to the Waterfront stage – the primarily puppet-cast “Avenue Q.” Princeton, the main puppet character, has just graduated from college and moved to New York City and quickly learns that life is not as easy as he has been led to believe by his parents and other authority figures.

He and his puppet friends struggle with finding jobs, finding love and finding purpose in life, all while singing hilarious and frequently un-PC songs like “Everyone’s a Little Bit Racist,” “It Sucks to Be Me” and “You Can Be as Loud as the Hell You Want When You’re Makin’ Love.” “Avenue Q” has been widely lauded as one of the funniest shows on Broadway, but be advised — “Avenue Q” is Rated R due to adult language, situations and puppet sex. This is not your average preschool puppet show. “Avenue Q” will run from Feb. 28 to March 25.

Next on the stage is “Good People,” a drama with dark comedic elements by David Lindsay-Abaire. In this play, Margie, a single mother living with her handicapped adult daughter, loses her job and scrambles to avoid being evicted from her Boston apartment. Her desperation for employment leads her to contact Mike, an old fling who has left South Boston, married, and become a successful doctor. Multiple misunderstandings and painful conversations ensue and the show ultimately illustrates how the most seemingly insignificant decisions determine our path. “Good People” was nominated for the 2011 Tony Award for Best Play and will run from April 12-29 every Wednesday through Saturday.

The last production of the season will be “Forever Plaid,” a musical written by Stuart Ross in 1989. On a stormy night, four singers who call themselves “The Plaids” meet their untimely ends when they collide with a bus filled with Catholic schoolgirls on their way to see the Beatles’ Americandebut on “The Ed Sullivan Show.” Miraculously, the Plaids return from the afterlife to perform their first and last show. The close-harmony soundtrack includes such 1950s classics as “Three Coins in the Fountain,” “Chain Gang” and “Heart and Soul.” The show has been called “laugh-out-loud fun” by The Wall Street Journal and has become an international success since its debut nearly 30 years ago. “Forever Plaid” will run from May 10-27 every Wednesday through Saturday.

Although the Waterfront does heavily utilize Key West’s rich pool of talent, the theater also works hard to bring many theatrical luminaries to town, including Terrence McNally, Carl Hiaasen and Charles Busch. When the theater is able to bring playwrights or original-run directors to town, the producers often host a “Talk Back” after one of the performances. At the end of the night, the guest star hosts a Q&A forum to discuss the play and the performance with the audience. Those special nights always sell out quickly and get rave reviews from participants.

You can read more about the Waterfront Playhouse’s upcoming performances, purchase tickets and learn about membership opportunities on the website at www.waterfrontplayhouse.org. And if you’re spending an evening at Mallory Square don’t forget, “When the sun sets, the curtain rises at the Waterfront Playhouse.”