Pines Profile: Bob Levine (b. 1933)
More Than Just An Entertainer
By Virun Rampersad. May 2026
Some people become part of a community. Others become part of its mythology. Robert “Bob” Levine, known to generations of Fire Islanders as the incomparable Rose Levine, belongs firmly in the latter category.
For more than seventy years, Bob has been one of the most recognizable, beloved, and enduring figures in the history of both Cherry Grove and Fire Island Pines. Today, he’s known for many things including a renowned drag performer, a successful businessman, a devoted lover of Broadway, a social chronicler, a dedicated fundraiser, the consummate host, and, invariably, the life of the party.
Bob is indeed all of those things, but he is also one of those rare people who is able to move effortlessly across different communities simply by being his authentic self. In this way, he has helped shape the culture, spirit, and social fabric of two of America’s most storied LGBTQ+ communities.
Bob Levine. Photo courtesy of Cherry Grove Archives.
A Boy from the Bronx Who Found His Paradise
Born in the Bronx in 1933, Bob came of age in a world where gay life was expected to remain hidden, coded, and cautious. Yet even as a young man he possessed an unusual confidence in his own identity. He had little interest in neighborhood games, preferring instead to spend time in movie houses and Broadway theatres, immersing himself in the world of fashion and performance. Long before he stepped on stage, he was already studying glamour, dialogue, timing, style, and character -- raw materials that he would later employ to make Rose Levine unforgettable.
Bob Levine. Photo courtesy of the Cherry Grove Archives.
In July 1955, a friend invited Bob to Cherry Grove for what was intended to be a brief visit. It didn’t work out that way.
“I arrived and I never left,” Bob would later say.
At that time Cherry Grove was primitive and defiantly bohemian. It was a place of kerosene lamps and outdoor pumps, populated by artists, actors, and gay people seeking a freedom that at the time barely existed. In era of institutionalized homophobia and harassment, Suffolk County police routinely raided the community, arresting men on vague charges of indecency. Those arrested had their names printed in the papers, ruining careers, relationships and sometimes entire lives. Despite this threat, Bob recognized that Cherry Grove was not just a summer destination, but a sanctuary and decided to put down roots. In 1965, he bought a home that tragically came on the market when the former owner was fired from his job after his employer discovered he was gay.
The Birth of Rose Levine
In that first visit, Cherry Grove not only captured Bob’s heart, but it also gave him his drag name -- his hosts greeted him with a sign saying: ‘Welcome Rose Levine!’
From there it was a short journey to becoming one of Fire Island’s most enduring and beloved stars.
The Arts Project of Cherry Grove is the irreverent cultural heart of the community. It was one of the few spaces in America in the 50s and 60s where gay men could publicly experiment with drag, gender play, camp performance, and queer expression with a degree of communal acceptance.
Bob Levine performing with Thom “Panzi” Hansen in Cherry Grove. Photo courtesy of Cherry Grove Archives.
When Bob began performing there as Rose Levine, he quickly distinguished himself from the camp caricatures common at the time. Rose was not only funny, but she was also polished, elegant, and unmistakably theatrical with black gowns, Broadway standards, sharp comic timing, and a ladylike sophistication. Unlike many drag performers, Rose does not lip sync; she sings in her own voice. And while her performances in the early years were not perfect – she was known to forget lyrics at times – her stage presence was impactful and memorable.
Rose Levine performing. Photos courtesy of the Cherry Grove Archives.
Not surprisingly, Rose Levine took off. What began as community entertainment evolved into legend. As social mores changed over the years, Bob would go on to headline at major venues, including the Ice Palace in Cherry Grove and 54 Below in New York City. He appeared alongside nationally known entertainers and built a following that stretched well beyond the Grove’s boardwalks.
As Michael Moran, President of the Arts Project of Cherry Grove noted:
“Bob is a top notch entertainer. You will never not have a good time at one of his shows. They are always fresh and engaging. Interestingly, he has become an even better performer with age, not forgetting lines and knowing how to deliver for his audience.”
Michael Moran, President of the Arts Project of Cherry Grove. Photo courtesy of Fire Island News
Bob’s success did not come effortlessly. Friends and colleagues all tell the same story: while he is no doubt a gifted performer, Bob has always rehearsed relentlessly and regularly introduced new content to keep the act fresh. He listens to audiences and always pushes himself to improve. It’s a discipline he has maintained throughout his life.
Bob Levine with Joel Maisano and Randy Riggs. Photo courtesy of Bob Levine.
This approach reflects a simple truth – Bob is not casual about entertaining. He appreciates that people are coming to see him and he puts in the work to ensure he doesn’t disappoint. Decades after he started, Guinness World Records recognized him as the world’s oldest performing drag artist, a distinction that says less about age than it does about the appeal of his work and his extraordinary stamina, discipline, and devotion to craft.
A Bridge Between Cherry Grove and the Pines
If Bob had remained simply a Cherry Grove drag icon, his place in Fire Island history would be secure. However, his influence grew larger because he became something comparatively rare in Fire Island’s earlier decades: a trusted and beloved presence in both Cherry Grove and Fire Island Pines.
When the Pines was developed in the 1950s, social tensions quickly emerged with Cherry Grove. Pines residents were generally more conservative -- and is some cases homophobic -- and many viewed Cherry Grove and its more flamboyant culture with condescension. For its part, Cherry Grove often saw the Pines as wealthier, snobbish, and unwelcoming. Few people moved comfortably between the two worlds.
But Bob did.
A natural people-person with deep friendships in theater, fashion, and business, Bob built relationships with early Pines residents, becoming a regular presence there while keeping Cherry Grove as his home base. He understood instinctively that despite stylistic differences, the two communities were linked by a common search for belonging, self-expression, and chosen family. Raised in New York and entirely comfortable moving through different social worlds, Bob was never intimidated by the Pines’ larger homes or greater wealth. At one point he even considered buying a house there, before ultimately deciding to stay in Cherry Grove.
As a man who had a foot in both the Pines and Cherry Grove it’s not surprising that Bob was present at one of the most historic moments in Fire Island, The Invasion of the Pines. On July 4th, 1976, he joined Thom Hansen (“Panzi”) and a flotilla of Cherry Grove drag queens and sailed into the Pines harbor in full regalia to protest a drag queen, Teri Warren, being refused service at the Blue Whale.
This action, at once defiant and theatrical, became Fire Island folklore. Bob later chronicled it in his Fire Island News column, christening it “The INvasion”, a play on the popular culture of the time. It became a hugely popular annual ritual that still endures today as a joyful symbol of queer resistance and communal embrace.
Bob Levine at one of the first Invasions of the Pines. Photo courtesy of Cherry Grove Archives.
Chronicler, Fundraiser, Community Man
Although Rose Levine is a legend in her own time, to reduce Bob to being an outstanding drag performer would be to miss his deeper significance. Bob is one of the most well-known and beloved people in both the Pines and Cherry Grove, legendary for bringing charm and energy to every event. In addition, for decades he has chronicled the social and political life in both communities for his column in the Fire Island News. A mix of social observation, humor, gossip and community updates, the column functioned almost as a living social diary fueled by Bob’s legendary network and wit.
Fire Island News coverage of the Invasion. Photo courtesy of Cherry Grove Archives.
But perhaps most importantly, Bob is known for his unwavering devotion to community. He began performing at charitable events in Cherry Grove as Rose Levine in 1955 and brought that same spirit to Fire Island Pines in 1981, appearing in a benefit produced by FIPPOA and the Pines Conservation Society in support of the Community Landmark Fund. For more than seven decades, he has used his talent, humor, and generosity not simply to entertain, but to bring people together and strengthen the communities he loves.When AIDS struck virtually everyone was impacted, Bob included – he lost his long-term partner, Larry Taylor in 1991. But like he’s done throughout his life, Bob kept pushing forward.
Larry Taylor with Rose Levine. Photo courtesy of Cherry Grove Archives.
Bob used his platform at the Fire Island News not only to document the devastating toll of AIDS, but also to promote the fundraisers and benefits that helped the community respond. His contributions, however, extended far beyond reporting. In 1986, he joined forces with John Whyte to stage benefits at the Blue Whale for Gay Men's Health Crisis and God's Love We Deliver, performing as Rose Levine.
For Whyte, who a decade earlier had inadvertently helped launch the Invasion by refusing service to a drag queen, it represented a remarkable evolution—one shaped in part by his longtime friendship with Bob. The events raised critical funds, lifted spirits, and gave audiences a few desperately needed hours of laughter and relief amid a time of profound loss.
Bob would return to that same instinct during the COVID-19 pandemic. Recognizing that isolation was taking its own toll on the community, he helped organize safe entertainment and social gatherings, providing the connection, joy, and buoyancy that people needed to endure another difficult chapter.
This is one of the clearest patterns of Bob Levine’s life. In virtually every situation, no matter how challenging, he seeks to entertain and bring joy to those around him. Its impact is undeniable. Diane Romano, former President of the Cherry Grove Property Owners’ Association put it this way:
“Bob is a phenomenal person. Authentic, caring and fun loving, he will keep you entertained for hours. He exemplifies some of our community’s best attributes – openness, welcoming, fun-loving, generous and kind.”
Diane Romano. Photo courtesy of Fire Island News.
Life Off-Stage
It is always insightful to look behind the curtain at a performer’s life to see what they are like when there is no audience and the theatre is dark. Close friends state that in Bob’s case, he is pretty much the same person – stylish, caring, curious and very social.
He has been together with his current partner Michael Fitzgerald for over thirty years, and together they have formed a chosen family. His friends note that with Bob ambiance is always a priority – he runs his fireplace in August. He also loves baking and his dinner parties are legendary in large part because of his extraordinary ability to make newcomers feel welcomed and old friends feel cherished.
Michael Fitzgerald with Rose Levine. Photo courtesy of Cherry Grove Archives.
Bob has a distinctive personality. Michael Fisher, creator of Cherry Grove Stories put it this way:
“Spend even a little time around Bob and certain qualities become immediately apparent. He is authentic, curious, welcoming, disciplined, generous, funny, elegant, and caring. He is an extrovert who genuinely delights in people. And while he is occasionally slow to remember a name, he is almost encyclopedic in his stories, even about chance encounters. He can recall what someone wore to dinner twenty years ago, and who introduced whom at what party.”
Gary Sacks, Mike Fisher, Bob Levine and Jeff Mahshie. Photo courtesy of Fire Island News.
Bob has a gentlemanly rigor to his demeanor. He compliments strangers, engages people warmly, dresses impeccably, and treats everyone with respect, while expecting the same in return. He has standards for manners, presentation, effort, and kindness. But these come not from vanity, but from a deeply held belief that communities thrive when people bring grace and consideration to one another.
Like all of us, Bob has had his fair share of disagreements with people and has fallen out with friends along the way. However, he will seldom shut a door permanently; he is almost always willing to make up and move on. As Bob himself notes (without irony) life’s too short to carry a grudge.
What surprises many is that although he is a very successful drag entertainer Bob did not make his living by performing. Indeed, he has for years donated his performance fee back to the Arts Project of Cherry Grove. Rather, Bob had a very successful career in the garment business, eventually opening his own company. His success here was driven by the same traits that made him a legend in Fire Island – intelligence, authenticity, curiosity, a sense of style and the ability to build strong relationships. He approached his business career with the same dedication and thoroughness as he did his drag performances. Indeed, he was often seen riding the early Monday morning ferry from Cherry Grove back to the mainland dressed in a business suit following a Sunday night show.
The Unstoppable Bob Levine
It is not unusual for talented performers to become celebrities in their own communities, but more often than not they fade into the background over time. Not so Bob. Now in his seventh decade on Fire Island, he remains as relevant as ever. As longtime Pines resident and well known architect, Hal Hayes put it:
“Bob Levine is nothing short of Fire Island royalty. Bob's alter ego, the superstar Rose Levine, has performed in countless productions at the landmark Cherry Grove Theater, scores of solo cabaret shows in the Grove, the Pines and throughout North America, was one of the participants in the original 1976 Invasion of the Pines, and stars in every annual reenactment since. Elected Queen "Rose" of Cherry Grove in 2018 and still going strong as the Guiness Book of World Record's oldest living drag performer, Bob/Rose is unstoppable, indefatigable, unforgettable.
Bob Levine at the home of Hal Hayes. Photo courtesy of Hal Hayes.
If there’s a secret to Bob’s enduring vitality it is his curiosity and positive attitude. While he has many cherished memories Bob does not live in nostalgia. Rather, he is fully present and is always looking to the future with optimism. Despite being in his nineties, there is something unmistakably youthful about him -- an aura that he is still interested, still evolving, and still delighted by life and by people. It is this, perhaps more than anything else, that gives him his timeless quality that underlies his personal appeal. He is someone you enjoy being around.
Born before the start of World War II, Bob has lived through a breathtaking era of social, cultural, technological, environmental, and economic change. Through it all, he has remained true to his core values, guided by curiosity, generosity, and a willingness to embrace what brought him joy.
The result is a life that has made him not only one of Fire Island’s most recognizable figures, but also one of its quiet architects. Through his example, his generosity, and his love of entertaining, Bob did more than make Fire Island more fun. He helped shape the culture of a community that values authenticity, creativity, connection, and joy.