My first memory of Jon Santos is from the year 2003. On a makeshift set in my lola’s house, he filmed a rendition of Charlene’s “I’ve Never Been To Me” as 21 different characters. I, a curious child, peeked from around the corner as he changed wigs and makeup, transforming from Vilma Santos to Miriam Defensor-Santiago to Erap Estrada to Austin Powers to Ice Seguerra over the course of an afternoon.

20 years later, I remind Santos about the video, bemoaning that it’s long been taken down from YouTube (perhaps Charlene’s label’s doing). The impersonations, each only a few seconds in the edit, are indelible in my memory. It remains an essential four-minute supercut of his range and breadth as a comedian.

Today Santos and I reunite to talk as he gets glammed up for this cover shoot. A conversation with Santos is a sprawl through history, a network of anecdotes and memory, but always making its way back to the lessons of his life. In this way, we make our way through an illustrious three-decade career on the stage and screen.

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Some brilliant things about Jon Santos:

1. Though our conversation ran two hours, he remembers everything. Three days after our shoot, I got an email with a WeTransfer link: Never Been To Me (Jon Santos).mov.

2. He brought a CD of Pet Shop Boys’ “Actually” to the cover shoot because he wanted his hair done like Neil Tennant’s.

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Santos’s work in comedy began around the EDSA Revolution, working on production staffs and playing supporting characters for his mentors Willie Nepomuceno and Tessie Tomas. It was an exciting time for political comedy. The end of martial law afforded comedians freedom of speech for the first time in nearly two decades. “So much of that we could not do before EDSA I,” he says. “I was already doing theater work at the tail end of the time when the administration [could] send people to watch your shows from the very back row and check what you were saying.”

With a ragtag group of friends who became his first producers, directors, and managers, Santos made his debut in earnest in a one-man show at Music Museum in 1988. “And then nagkaroon na ng brand: This is like if Tessie Tomas and Willie Nepomuceno had a child,” Santos says. “He was an equal opportunity impersonator: men, women; equal opportunity offender: both sides of the political fence. That was my training: Play everybody, play anybody who’s on the news.”

Over the course of his career, he’s parodied every occupant of Malacañang since Ferdinand Marcos Sr., Filipino celebrities beloved and loathed alike, even news personalities who were a blip in the press cycle (Janet Lim-Napoles, anyone?). Santos has always worked towards these characters with a signature rigor. “You always end up discovering a ground you share,” he says. “Because as an actor servicing a script with this character, there’s always this truthfulness in the imagined circumstance that you aim for. So you cannot help but make it like a Burger McDo where the bun is the Miriam or Ate Vi or Erap character and the burger is still you.”

As many comedians do, Santos discovered his funny bone even earlier in life. He reminisces about elementary school as a class clown. “When the teacher’s not looking, imitate the teacher. So even then I think I had my first taste of eliciting the ‘Oo nga ano? Mrs. Ganito walks like that. Oo nga ano? Mr. Concepcion talks like that. Oo nga ano?'” he says. “The truth teller who uses parody and imitation and a spoof to sugarcoat truth with levity — sorry, ang pretentious.”

Deflect as he may, this is the heart of his work in political comedy: Speaking truth to power, offering a funhouse mirror reflection of reality, equal opportunity offense. “It does not include telling you what to do. It also does not include telling you what I would do.”

A year ago, however, Santos retired from comedy. At his final show “LiveScreaming,” each of his beloved characters said goodbye. The decision was the product of many life changes, with Santos primarily needing to care for his aging parents and the orphaned children of his late sister.

In the time alone with his husband West Stewart over the pandemic, he also found himself at peace with a life of purpose and balance. “Because I really had 40 years of fantastic drag moments on stage, people smiling. Parang kumota ako sa fulfillment and joy of bringing life to these characters onstage,” Santos says. “My hairline and my skin and my lower back paid the price. We are really not made for high heels.”

At the same time, the political landscape had also grown far more divisive. While Santos was used to playing the room at election-themed shows every six years, he found himself among a tougher crowd in 2022. “So you’re working a room and there’s half of the room na [pro-Robredo] and this other half of the room na [pro-Marcos] and it just gets a little tricky. The decision [was] to do ‘LiveScreaming’ as a welcome back from COVID. ‘Yun na lang! That is the only ground we share.”

The pre-show announcement would also request audiences not to film Santos’s performances, but this rule had become harder to enforce. “Everything’s about nuance and context... but now it gets trickier and trickier and you get the wrong kind of meme for the wrong kind of line and it’s really something I’m a little too old to deal with,” he admits.

I wonder whether his relationship with comedy has grown fraught, but all Santos feels is grace. “Honored to have been given the open doors, grateful that I was guided and mentored to have enough skills to pull it off all those years, like three and a half decades,” he says. “It’s very, very consuming but I would like to think I was built more than I was consumed. They say passion consumes, love builds. So the love was bigger, the love from the audience came back to me.”

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3. ‘Di siya nagpapatawa off-camera. “Don’t you hate it when people say, ‘Crack a joke naman’? That’s the best way to offend Tessie Tomas or Willie Nepomuceno,” he says. “These are characters I play. I am an actor. My husband doesn’t wake up to Miriam next to him. The makeup is off, this is a job.”

4. His favorite Italian saying is: “We laugh so as not to cry.” He explains, “The same curveball, the same card that life deals you, madalas nakakaiyak but you could deal with it with laughter… I have learned to see more than one side to anything at meron at meron kang mapagtatawanan.”

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The surprise, or as he calls it, “the latest punchline of the universe,” was what followed his intended semi-retirement. In the last year alone, Santos has been booked for more on-camera work, which he found he could balance better with his new roles in life. He sat as a judge on the first season of “Drag Race Philippines” (and the forthcoming second season). He acted as a drag mother in JP Habac’s iWantTFC series “Drag You & Me” alongside local Drag Race alums and original members of the Paper Dolls, a legendary drag group from the ‘70s.

Up next is The Sandbox Collective’s staging of Duncan Macmillan’s “Every Brilliant Thing,” a one-man play translated into Filipino by Guelan Luarca, which Santos is in rehearsals for now with director Jenny Jamora. The play follows the Narrator who begins listing thousands of “brilliant things” after his mother attempts suicide. After that, Santos makes his QCinema debut as the lead in the short film “Abutan Man Tayo ng House Lights,” where I’ll be directing him. In the film, two middle-aged gay men reunite by chance at a rave in the year 2044.

He ventures out into new territory with the same rigor, searching for the truth in the imagined circumstance of every character he needs to play. “I’m happy, though, to set [comedy] aside if new dreams are opening up and new challenges are there, like [‘Abutan Man Tayo ng House Lights’]. Letting your eyes say ‘I will be free of you!’ in ilang frames per second. That’s so new!” he says.

He explains the detail with which he’s delved into the world of “Every Brilliant Thing,” developing a meticulous timeline of the Narrator’s life, writing his own brilliant things every day.

It takes a visit to their rehearsals to really see the breadth of his work with Jamora. The script, which requires many moments of improvisation and audience participation, feels like a living, breathing thing. I see Santos and Jamora rewriting on the fly, discovering new details and emotional threads, translating the Macmillan text both culturally to the Philippine context and rooting it emotionally in Santos’s own world. “He’s his own dramaturg,” Jamora says, noting how Santos’s years of experience as a writer helped them develop the adaptation.

Santos is quick on his feet in rehearsal, pausing to rewrite and fine-tune timing, easing his way towards the stage version we’ll see in July. He says he finds himself so deeply enmeshed with the work, recalling that Jamora wanted to see “you, but not you” in his take on the Narrator: a discrete character yet one closer to Jon Santos than we’ve ever seen Jon Santos be.

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5. In rehearsal for “Every Brilliant Thing,” he mentions that the Narrator lives in Poblacion. I say, “Wouldn’t someone from your generation call it ‘Backwell?’” So now Backwell (Back of Rockwell) is in the script.

6. While working on this story, I mention Jon Santos to a friend and he remembers Santos as the first person he ever saw in drag on local television. We get to wondering whether female impersonation in comedy was drag’s entryway into mainstream Filipino media in the ‘90s.

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“Drag Race Philippines” made for an exciting reintroduction for Santos to a totally new audience of viewers. He says it was the first time he was booked not as a character but just as Jon Santos. He says, “Na-curious ako na, sheesh, 35 years in drag and I never trended! Here I am, I put on a suit, I just talk about, ‘Um, that wig was a little unwieldy, right? And the shoe choices,’ and it trends! I felt so much love.”

Coming on the show was a full circle moment for him. He says, “There are more people doing what I used to do and they saw me as someone who can be part of this community in another way, as an alumnus.” Though he takes on this role today, he’s mindful of his place in a rich lineage of queer Filipino entertainers. “I do remind them that I also stand on the shoulders of Fanny Serrano, James Cooper, the Paper Dolls, Babette Villaruel, Manny Castañeda, Bernardo Bernardo and all those who broke the ceiling before my batch,” Santos says.

“[Ang ] sarap to know that there was value to that bulk, to the mid-‘80s to early 2000s body of work, that included drag,” he adds. “I really am reminded by these young kids that there was some angas to making that decision in the mid-‘80s. ‘No, no, I’m gonna do this on primetime, I’m gonna do this in a sitcom, I’m gonna do this on noontime,’ which is to not be in men’s clothes.”

While popular drag has evolved over the decades, it’s easy to find traces of Santos’s era of impersonation in the form. I remind him that his work was “RuPaul’s Drag Race” Snatch Game before Snatch Game was a thing, and he says that witnessing the new generation of drag artists has him “very, very happy and relieved that… Pinoy drag and Pinoy comedy is in good hands, and legs, and shoes! Ang tatalas, and I was so surprised. Marina Summers and her Gloria, waaah! There’s stuff in the new season I cannot talk about. The character choices, the edge work, it’s so impressive. They’ve got angas.”

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7. The first proof he has of himself in drag is a photo from 1973. He was seven years old and going to an all-boys school meant he got all the girl parts. “I had a Shakespearean journey very early,” he says. “Pag Linggo ng Wika, I was the one in the kimona because I think I had small pores, and I had fair skin, and I was fay and I was soft.”

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We talk about growing up LGBTQIA+ in a conservative Filipino household, how silent acceptance is possible, and can be a decent if imperfect scenario for queer youth. He recalls that his parents were “very Catholic and very military” but there was no drama or discussion around his sexuality. “Wala akong coming out monologue to this day,” he says.

After Santos married Stewart in 2005, his parents didn’t find out until the story came out in the papers. “They were already seeing him join me when I’d visit. After a while, I’d come to the house without him and they’d say, ‘Asan si West?’ So after a while, nare-realize mo, hindi naman pala ine-explain lahat ng bagay. We just lived it,” he says. “And I’ve always believed that their love was bigger than their questions.”

Today, he finds himself in the position of queer elder to younger family members who come out to him and seek his advice, as well as young queer people in the entertainment industry. “It’s nice to hear something like, ‘I was less afraid to do this because my parents knew of you,’” Santos says.

He recalls starring in the Eraserheads jukebox musical “Ang Huling El Bimbo” as Anthony, a character struggling with his identity. “I kept thinking: What if there are parents here who had children that they were noticing na medyo iba? Na may sikreto? What if there were parents who learned to investigate differently because they knew of someone like me who got by and who found purpose and happiness and joy being himself and following his passion?”

He wonders aloud what qualifies him for this cover story. “What made them look? Narito lang naman ako,” he says. It feels again like an underestimation of what his presence all these years has meant, how he’s survived and thrived in spite of a society that threatens the obliteration of LGBTQIA+ people at every turn.

It can be difficult for LGBTQIA+ people to imagine futures in a society so hostile to our existence. We’ve lost so many of our queer elders to violence and neglect. Yet in a life like Jon Santos’s, we can imagine what’s possible if we fight it out and stick around — present survival as the promise of a future. We stand on shoulders like his.

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8. Santos has a sharp memory. Enough to carry a one-man play, enough to pin down each of his own life events down to the year. His stories point to a rich relationship with time.

9. I ask what he’d tell the Jon Santos who started all this over 30 years ago. All he says is: “Kapit. It’s gonna be okay. And I will not stop telling, because I tend not to listen to that. I tend to listen to the other voices. I will never underestimate the importance of that reassuring voice saying, ‘Kapit, it’s gonna get better’… and then it’s gonna get not-so-better. And then it’s gonna get better.”

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Santos’s cover of “I’ve Never Been To Me” ends with him as Ate Vi singing, “And do you want to see the real me? Alright, this is me.”

Santos admits that his childhood imitations of authority figures revealed something beyond just his nascent comedy chops. “It’s also that I didn’t want to be me. Eaugh!” he says. “There was this need to be someone else and then you felt so powerful and also when you’re imitating your teacher, you make everybody look.”

These days, however, he gets to look back at his own history with an enviable warmth, even kindness towards his past self. “Of late, there’s so much love and enjoying, it kind of glosses over the bwiset and the abala of all the years of taking a cab as Jon Santos and leaving the cab looking like Ate Vi already. You just have your gown in your backpack, and you put on your eyelashes in every stoplight kasi it’s steadier. There were really, really tough years before I was financially comfortable but I would do everything all over again.”

“They said before therapy your life was a dark room and you’re bumping into the furniture. For the last 35 years, I don’t bump into the furniture! I get better and better at not bumping into the furniture, but the room is still effing dark to this day!”

It’s been wonderful to meet the Jon Santos behind the characters in the last few years, to see him unafraid to be himself. I ask what got him here and he’s quick to answer “Therapy!” He adds, “They said before therapy your life was a dark room and you’re bumping into the furniture. For the last 35 years, I don’t bump into the furniture! I get better and better at not bumping into the furniture, but the room is still effing dark to this day!”

Learning not to bump into the furniture comes with the passage of time and Santos’s constant introspection and examination of his life. “You inspect every day if you’re dreaming the same dreams,” he says. “Maybe it shifts every day. Maybe we should all investigate every day.”

To this day, he continues to discover himself, continues to ask questions, continues to find brilliant things in the dark room. Though he once said he’s “never been to me,” he’s definitely making his way there.

Jon Santos stars in “Every Brilliant Thing” at the Sandbox Festival from July 13 to 15. Tickets are available here.

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Photos by JL JAVIER
Styling by NEAL CORPUS
Hair and makeup by SYLVINA LOPEZ
Cover design by THE PUBLIC SCHOOL MANILA
Video by SAMANTHA LEE
Produced by DON JAUCIAN and GABY GLORIA