Philip Bailey loves putting on a show. He is considerably less enthusiastic about the pantyhose, makeup, wigs and high heels required to appear in one. As Cassi Phillips, the iconic Riverside drag performer and producer has spent decades helping shape a scene that owes much of its vibrancy to his imagination and commitment. From intimate bar performances to elaborate productions at the Riverside Municipal Auditorium, Bailey has brought performers together, nurtured emerging talent and helped expand audiences’ ideas of what drag can be. His influence reaches well beyond his own time in the spotlight, into the careers he has encouraged and the community he has helped build.

As his 60th birthday approaches, Bailey is preparing for an unusual role: being the center of attention at a show he has not had to organize. Friends are putting together “The Roast of Cassi Phillips” at the Menagerie on Sept. 20, and he has deliberately kept himself out of the planning. For someone accustomed to choosing the cast, arranging rehearsals and assembling the production, the chance to simply show up and enjoy the evening is a gift in itself. “It is an art form that I love to my core,” Bailey said.

His introduction to performing in drag came as a teenager in In Another Dimension, a “Rocky Horror” shadow cast whose members acted out the film in front of the screen. During a switch night, when the cast traded gender roles, Bailey played Columbia. Small and young, he recalled surprising audience members who had not realized a boy was playing the part. Their reaction caught his attention as much as his performance caught theirs, and what began as dressing up opened the door to something much larger.

A fellow cast member later brought him to an Orange County bar, where seeing a drag show in person introduced him to a world he had only glimpsed on television. He befriended performers, like Pauline St. James, and eventually found himself directing a “Rocky Horror” production featuring established local queens. He was still a teenager, but the performers around him welcomed him into their circle, teaching him makeup, hair, clothing and the work of being an entertainer.

That education came with mentorship and protection. Bailey recalled the older queens refusing to let him drink and keeping adults who took an inappropriate interest in him at a distance. His drag mother reassured his parents that they were looking out for him, and his parents allowed him to remain part of a community where he felt understood.

“They didn’t kick me out of the house,” Bailey said. “I still lived at home.”

By early adulthood, he had already spent years learning the craft. He developed a specialty in lip-syncing spoken comedy routines, finding a place for himself through timing, personality and an ability to work a microphone. Hosting eventually led him toward the part of the job he enjoyed most: building the entire show, from its lineup and choreography to the way performers worked together.

That interest would become central to “Fant-a-Shes,” the production he brought to the Riverside Municipal Auditorium. Bailey was working in the auditorium’s ticket booth when his then-boyfriend suggested staging a drag show there. He gathered a group of performers whose celebrity impersonations could fill a theater with familiar characters, but the idea also grew from a frustration he had encountered among people who worked in traditional theater.

When Bailey described himself as an entertainer, he said, some treated drag as something less legitimate than their own work. Meanwhile, he and his fellow performers were assembling ambitious shows in small bars, combining production numbers, duets and comedy with limited space and resources. “Fant-a-Shes” offered a chance to show a larger audience what they could do. “If somebody gave us a chance, look what we could do,” Bailey said.

Getting that audience into the auditorium took some help. Bailey recalled slow early ticket sales, followed by a connection that brought a Press-Enterprise reporter to rehearsal. A substantial newspaper feature followed, and suddenly people were lining up at the box office. He remembers the first production bringing together eight performers for a two-and-a-half-hour show featuring roughly 17 celebrity illusions.

The response changed how the cast saw themselves. Bailey recalled people recognizing them on the street after the show, and other performers soon wanted to join the production. What had started as an opportunity to prove themselves became a show with a following of its own.

After its original run, Bailey stepped away, exhausted by the demands of producing it. Years later, interest from Live Nation helped bring “Fant-a-Shes” back to the auditorium. Bailey said the revival sold out, welcoming returning performers alongside newer faces and drawing an audience that had not forgotten the show.

His other productions explored different possibilities for drag. Inspired by the television variety shows he loved growing up, he developed an ensemble show that mixed scripted comedy, live singing and lip-syncing. He also wrote jukebox musicals, continuing to look for ways to build something beyond a succession of individual performances.

Along the way, he has made room for newer entertainers. Bailey recalled giving Raven a solo spot in “Fant-a-Shes” when she had been performing in drag for only about eight months, recognizing an originality he wanted audiences to see. He does not describe himself as a drag mother with a family of performers carrying his name. “Auntie Cassi,” a nickname others have given him, is closer to the role he enjoys: offering encouragement and a place to develop.

His attachment to that community includes memories far more difficult than rehearsals and opening nights. Bailey was already going to bars when he first heard about the illness that would become known as AIDS. He recalled losing friends throughout the 1980s, attending funeral after funeral and seeing drag performers raise money for people whose families would not help bury them.

Even now, he struggles to reconcile the happiness he remembers with the scale of the loss surrounding it. The friendships, performances and sense of belonging were real, as was the grief. Having lived through both informs the way he speaks about the community’s endurance and the importance of places where people can feel comfortable being themselves.

Riverside became that kind of home for him. When he moved here, Bailey was struck by the strength of its gay community, and he has remained committed to making work here rather than pursuing a bigger name elsewhere. He appreciates what “RuPaul’s Drag Race” has done for friends’ careers, but national fame was never his goal.

“I’m far happier being that person in the background that supports others,” Bailey said.

For now, Bailey wants a substantial break from the demands of “Fant-a-Shes.” He is unsure whether there will be a production next year, though he is not ruling out returning. He described the latest show as one of his favorites, but putting it together requires months of work. He also emphasized that bringing independent drag artists into an ensemble production asks them to work differently from the solo performances they are used to, while balancing the strong self-belief that helps them succeed onstage.

There are other things he wants to explore, including a murder mystery he has started writing and, eventually, a book about his early experiences in drag. He does not have every next step planned, and for once, that seems to be part of the appeal.

The birthday celebration offers a more immediate opportunity to let someone else take charge. Bailey provided the organizers with names of people from different chapters of his life, including his sixth-grade best friend, then asked to hear nothing about what they were preparing. Even his husband’s planning calls have been kept out of earshot. He knows people have been working on the evening for months, but not who will appear or what they will say.

“I’m really excited to be an audience member of something,” Bailey said.

Riverside will have a chance to join him when “The Roast of Cassi Phillips” celebrates Philip Bailey’s 60th birthday at the Menagerie at 8 p.m. Sunday, Sept. 20. Come out to support an entertainer who has spent decades creating opportunities for others and helping make Riverside’s drag community a place to belong. This time, he gets to sit back while the people who know him best take the microphone.