By Laura Richardson

Between the myriad live music options, multiple nightly drag shows and general nightlife temptations, choosing an activity when you visit Key West can be a daunting task if you don’t know where to start. Those in the know, however, typically begin their planning by checking out a tried-and-true option for world-class entertainment: The Waterfront Playhouse.

Located in a gorgeous brick historical building on Mallory Square, the Waterfront Playhouse consistently features shows and performances of a caliber one wouldn’t necessarily anticipate finding on a two-by- four-mile island, yet every season is consistently more exciting than the last.

Dubbed “the Best Professional Theater in Florida” by Florida Monthly magazine, the Waterfront Playhouse is a not-for-profit professional theater. It has been at the forefront of bringing cutting-edge theater straight from Broadway to Monroe County since its inception. This season marks the theater’s 78th 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 that included locals and Navy personnel who put on theatrical productions wherever they could find space to perform. This often included unconventional locations, such as the submarine tender U.S.S. Gilmore, which was docked in Key West after World War II. The Key West Players moved into their current location in 1960. The building served as an ice warehouse in the 1880s.

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. Danny 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 playhouse, as well as multiple concerts and special theater events. In addition, he is an immensely talented actor. Before he graced the Waterfront stage, Danny 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 City and at the Smithsonian in Washington, D.C. At the Waterfront, Danny 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 Danny’s creative vision and vast production experience and talent.

The Waterfront Playhouse begins every season with a grand kick-off concert that features local vocal talents and typically adheres to a particular theme, often highlighting a musical artist or cultural event like the Academy Awards. This year, the concert is this weekend, Nov. 17-18, and features Danny along with the immensely talented vocalists Laurie Breakwell and Vicki Roush. This triple threat of singers will entertain the crowd with Broadway hits from shows across the Great White Way’s history, including “A Chorus Line,” “Cabaret” and “Hamilton.” Opening night tickets run $70 and include a post-show, catered party to celebrate the official start of the season. Tickets for Saturday are $50 and you’ll have to have your own after party (and we have no doubt you’ll have great success in that endeavor).

As the Waterfront grows and expands its repertoire, it’s not uncommon to hear Danny say that this is one of the most ambitious seasons in the storied history of the playhouse. After this weekend’s concert, the first official production on the Waterfront’s calendar is “Inspecting Carol” by Daniel Sullivan. This show-within-a-show comedy, written in 1991, concerns a struggling theater company in danger of losing its NEA funding. In order to entice audiences to attend its holiday performance of “A Christmas Carol,” which is already in jeopardy due to a dysfunctional cast, the company adds a few inappropriate twists to the beloved Charles Dickens classic. As is to be expected, Danny has cast many of Key West’s most revered comedic talents, including the adorable Annie Miners, the ridiculously goofy Mathias Maloff and slapstick professional David Black (these names are just the tip of the iceberg, by the way; this cast is a who’s who of Key West’s funniest). Although irreverent, the play is family friendly (despite some very mild profanity) and would be an excellent way to spend a festive evening out on the town. “Inspecting Carol” will run from Dec. 12 to Jan. 6 every Tuesday through Saturday.

The next show on the schedule is the iconic musical “1776,” which I swear has been running on Broadway since the Declaration of Independence was signed (and for good reason). With music and lyrics by Sherman Edwards and a book by Peter Stone, “1776” was the recipient of the Tony Award for Best Musical in 1969. The musical centers on the efforts of John Adams to persuade his fellow colonial statesmen to rally behind American independence, a difficult task made more so by the deep regional divisions between our nation’s forefathers. Although the show was written in 1969, the ideological political divide is a theme that still resonates in today’s landscape of current events. Much like “Inspecting Carol,” “1776” has an all-star cast of 25 people and will be presented in a concert setting with an eight-piece orchestra, making it one of the largest shows ever produced by the Waterfront. The cast is nothing short of impressive, including the versatile J.B. McLendon as Benjamin Franklin, Tom Murtha as John Hancock, and the inimitable Laurie Breakwell as Abigail Adams. “1776” will run from Jan. 24 through Feb. 4 every Wednesday through Sunday with a low-priced preview on Tuesday Jan. 23.

After the daunting yet successful and hilarious undertaking that was “Avenue Q” last season, it seemed like the Waterfront Playhouse would never want to engage in felt-based theater again, but in a move that has shocked and delighted all of us, the Waterfront is staging not one but two puppet presentations — the five-time Tony nominated and immensely critically acclaimed “Hand to God” and the primarily puppet-cast, filthily hysterical “Avenue Q ,” which is back for a second tour on the Waterfront Stage.

“Hand to God,” an outrageous comedy by Robert Askins, has been billed as “Sesame Street” meets “The Exorcist.” Three troubled teens attend a Christian puppet ministry where Jason, one of the students, creates a hand puppet named Tyrone, who declares that he is Satan and disrupts the devoutly religious Texas town. The New York Times called “Hand to God” “ferociously funny,” and there is no doubt that the Waterfront’s cast will live up to that billing. “Hand to God” will run from Feb. 20 to March 10 every Tuesday through Saturday. There is definitely a lot more than mild profanity in this show, so maybe leave little Timmy and Britney at home with the sitter on this one.

In “Avenue Q ,” Princeton, our poor puppet protagonist, has just graduated from college and moved to New York City, where he learns very quickly that life is not as easy as he has been led to believe by his parents and other adults. 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 such as “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 that “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 March 27 to April 14 every Tuesday through Saturday.

The last production of the season will be “The Legend of Georgia McBride,” a comedy with music written in 2015 by Matthew Lopez. Casey is a young and struggling Elvis impersonator living in the Florida panhandle with his pregnant wife. In a desperate attempt to make some fast money one night, after his Elvis show gets canceled, he fills in for an intoxicated drag queen and discovers that he is a natural lip-syncing talent in heels. The Waterfront production of “The Legend of Georgia McBride” will feature Key West drag sensation Christopher Peterson, who is not only beloved locally but also revered on stages the world over. The show has been called “stich-in-your-side funny” by The New York Times and is chock-full of “funny-bitchy repartee.”

“The Legend of Georgia McBride” will run from May 2 to May 26 every Wednesday through Saturday.

In today’s often tumultuous times, it is always a comfort to know that there is somewhere you can go for a good laugh and an escape for an hour or two. This season, more than most, Danny has gone above and beyond to bring the funny to Key West’s theater scene, and I have a feeling that, come May, anyone lucky (and smart) enough to catch a performance at the Waterfront Playhouse will be smiling a little wider and laughing a little louder than the rest. And, as Dickens himself wrote in “A Christmas Carol,” “There is nothing in the world so irresistibly contagious as laughter and good humor,” so we’ll all have Danny to thank as we laugh our way through the season.

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