The Caftan Chronicles

The Caftan Chronicles

The Irrepressible Jessay Martin Is One of The 4 (Sometimes 5) "Old Gays" of Social Media Fame

Already friends with him, the preexisting Old Gays asked him aboard to increase "diversity." He also brought his mega-smile, his joy, his cancer journey, his singing voice & his love of Patti LaBelle.

Tim Murphy's avatar
Tim Murphy
Jan 13, 2025
∙ Paid
Photo of Jessay from The Old Gays Instagram account.

Happy January, Caftaners. I have to address the L.A. situation first. My jaw is on the floor watching what's happening there. It's hard to think of a U.S. weather event or natural disaster exacerbated (if not necessarily caused) by climate change as stunningly devastating and sweeping as this. As an L.A. friend who grew up there texted me the other day, "Whole swaths of the city, with all their history and landmarks and memories, are being leveled."

I am just agog at the scale of devastation, loss and displacement. For us in this little Caftan community, if you know of anyone, particularly queer and/or financially precarious who's been made homeless by this situation and has started a GoFundMe that lays out what's happened to them, please send me the link so I can post it on Caftan and perhaps help add to that person(s)'s relief fund. Email me at timmurphynycwriter@gmail.com.

Now I'll switch to something much lighter and, well, more Caftan. So at the top of my last post, if I remember right, I said I had an interview with a big icon coming up. So now I'll tell you who it is and why it didn't happen: It was the legendary costume designer Bob Mackie—someone I've been trying to get for Caftan for a while. There is a pretty good new documentary about him called Naked Illusion that is now available to stream.

So when I heard about it, I went through the film's publicist, who I think is also Bob's personal PR. I had to follow up a few times but the PR finally asked if I wanted 30 minutes (not much time for a Caftan interview!) with him, and also told me I'd have to submit the questions in advance so he could think about them. So I watched the documentary, which frankly only glosses over Bob's life as a gay man and his relationships, and then sent the PR a very honest email, part of which goes:

"So in terms of questions for Bob - well, first of all, if I could get 40 instead of 30 minutes that would mean a lot - but more importantly, as I told you, The Caftan Chronicles' primary audience is older gay men (my age, 55, and up, largely) who I'm fairly certain are familiar with Bob and his work, and who will see the doc, all the more so after I rave about it. But the thing is, I want to interview Bob as a gay man, which is only briefly touched on in the doc. I don't want to ask him the same dumb questions like "What was your favorite dress you ever made?" or "What legend did you like working with best?" Those are not interesting to me. I want to talk to him about his life and career in the context of his being a gay man. (And these are questions I often ask in my Caftan interviews:) When did you first have gay feelings and how did they make you feel? Who were your earliest gay crushes or even relationships? What was the prevailing discourse in Hollywood when you started in the early 1960s about gay folks in the industry, and when did you start noticing a change toward more openness? Not until the 70s? Or even the 90s?”

I went on in that vein about what I wanted to ask him, even as I guessed—given the fact that Bob, in life and in the documentary, is unfailingly gentlemanly and good-natured but also (in a very old-Hollywood kind of way) seems to lean away from true candor, especially about personal and uncomfortable stuff—that Bob and his PR would decline this kind of interview.

Well, I was right. The PR indeed declined—politely. (I'd love to know if she even ran my request by Bob or merely decided for him that this wasn't the kind of interview with him that she wanted out there.) I wasn't surprised by the decline. I said that if Bob was ever up for a different kind of interview, I'd love to do it.

But I tell you this story because I hope it demonstrates that I don't ever want to do a pat, surface, boring interview for Caftan—with anyone. I guess I could've done and run a short interview with him where I asked him some softballs like "What's your favorite costume you ever made?" or "Who was your favorite diva to work with?" (He'd probably have found some charming and deft way of dodging even that question.) But no. That's not why I started this project. I'd rather do a substantive and honest interview with someone less iconic and branded than a Bob Mackie. I started this to try to get older gay men to talk with ruthless honesty about their lives, as a kind of roadmap for the rest of us, or whatever. Not to do the kind of 30-minute surface interviews I've often paid the rent with these many years.

So anyway. Now I will set up the interview that I did do this week. It's with Jessay Martin. Have you heard of The Old Gays? They are these four (sometimes five) senior gay men in Palm Springs who have kind of become social (and even traditional) media darlings since around Covid for their Instagram and TikTok (which I'm not on) posts where they dance and talk and dish and do things. Here they are a year ago talking about their “in and out” list for 2024, this time including Old Gay #5, Joc (Filipino guy in the upper left), who is Jessay’s longtime best friend:

The Old Gays’ stuff is clearly kind of professionally produced but it's still really charming and in a way a kind of advertisement for Palm Springs as this really fun place for gay men (who can afford it, 'cause it's not cheap anymore!) to retire to and have their final chapter of fun and familial friendships. They have a book out, too, called The Old Gays Guide to the Good Life: Lessons Learned About Love and Death, Sex and Sin, and Saving the Best for Last. (What kind of senior gay book would it be if it didn't reference a Vanessa Williams song?)

The Old Gays are (left to right) Bill, Mick, Jessay and Bob.

I spent some time watching TOGs and decided to ask Jessay Martin, the second youngest at 71, to chat with me. I loved that he seemed both sassy and very sweet. So what follows is our two-hour interview we did on Jan. 10. Jessay, who has been a professional singer his whole life, is a nut in the best way. (I was not surprised at all that his favorite diva is Patti LaBelle, who is also one of my favorite divas because she just seems like such a ham in the best way, someone who—despite her prodigious talents—loves to make people smile and laugh and doesn't take herself too seriously and can be, well, a big goofball.

(Do you remember when Patti LaBelle wasn’t given either her background singers OR the right lyrics for “This Christmas” and vamped and mugged and joked her way through the song?)

And Jessay's like that, too. But with such a softness and a sweetness. He talks with great fondness of his mother and I can see how his mother shaped him. It's a great interview, even though at one point he told me to stop prefacing every question with, "Now, can I ask you this?" (This is an interviewing tic of mine.) So that became a bit of a joke between us because I kept on doing it and stopping myself, until he finally told me he didn't care.

So I hope you like it. I hope you've noticed I've been trying to post a chat about weekly because, in my attempt to grow this project (and it is growing, thanks to all of you), I want people who pay $5 a month for it to feel like they're getting their money's worth. Plus, honestly, doing these interviews is the highlight of my workweek and if I could, I would do one every day and just do Caftan full-time (aside from novel-writing). And perhaps I'll get there soon! In other words: Please consider upgrading to the paid version if you haven't already!

And oh! Finally I’ve figured out how to make audio clips out of my interviews. So here are two clips with Jessay—one talking about how he joined The Old Gays shortly after they began, and another about sex (and porn!) after having prostate cancer! (You can hear me typing madly in the background.) Let me know if you want more clips like this…or perhaps even full audio of the interview.

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Here’s Jessay Martin for you...see you again soon!


Jessay, thank you for agreeing to do a Caftan interview—I'm honored. Would you agree that you are the sassiest of TOGs?

That's probably a tie between Mick and myself.

Mic is quite the muscle stud.

Yes, he is. He has a gym in his home and that is his church.

Muscle Daddy Mick (from TOG Instagram)

Do you exercise or work out?

Well, right now I'm in physical therapy for foot surgery, so I've started walking a bit. I can only walk about a block and then I'm spent and have to come home and sleep. That's how exhausting it is. I've been down since August so it's been a longer journey than the doctor and I expected. The problem was tendonitis.

jessay.l.martin.12
A post shared by @jessay.l.martin.12

(Jessay talking about his surgery ^^)

But you have to walk as part of the recovery?

Yes, if you want to walk again, you just do it. I've been walking for about two weeks now.

How is the weather for walking in Palm Springs right now?

Well [laughs]...I like spring here best. It's in the lower seventies today with sunshine, so I can't complain.

Especially compared to L.A. right now. Do you have friends there?

I have one friend who lost his beautiful huge home in Pacific Palisades. Everything is gone except the walls because it was built of brick or rocks. My family has been calling me, asking How are you? I was like, I'm fine. I had no idea what was going on in L.A., and then they told me. So I told them that L.A. is about three hours away from me. I also have friends in Glendale [in L.A.] so I'm waiting to make sure they get out okay.

Okay, so Jessay...is that how I pronounce it, jessAY?

Yes. It makes you smile! My name is Jesse, but...do you remember Jackée from the TV show 227?

Of course.

That's where I thought up Jessay. I said, "This is me!" I started that when I moved to Palm Springs in 2013. My name was boring me. Four of us in my family have the name Jesse.

Also, Jessay Martin distinguishes you from the actor Jesse L. Martin.

I know him. I met him before a performance. He's the kind of person who, as rich as they are, they're down to earth.

Okay, cool. So what is a typical day like for you?

I wake up about 8am. Because of my foot surgery, I sit with a foot stretcher for a hour. I do this three time a day along with Netflix! Netflix! Netflix! Netflix!

I take it you're watching a lot of Netflix.

A teeny bit. [laughs] I also have rehearsals Tuesday nights. I'm in the Palm Springs Gay Men's Chorus and I also sing at different churches around town. (Here is Jessay singing at a Dallas megachurch that invited him to sing about six years ago:)

What else do you watch on TV?

I'm watching GMA right now. I love my Robin [Roberts]. I really love her. But I like 'em all. George Stephanopolous looks like a little baby that you want to shake!

Haha. I love Robin too. She just emanates "good person," doesn't she?

Totally. And calm. Watch her. She breathes before she says something. She lets the air out and then she talks and it's just calming. My mom never raised her voice but she had so much power. So I speak like that, too. [low voice] Down here. I'm every woman! It's all in me!

Okay. So then what do you do?

Get up and make my breakfast and then read and then rehearse my voice and then back to Netflix. I love this show Glow Up. A competition show for makeup artists.

Have you watched Emilia Perez?

Not yet. I also do movie night with my buddy Ernie. He picks the movies and they're all really good. We don't do heavy stuff. I try to watch uplifting fun stuff to keep from getting in my head about the messes that are going on in the world.

I also go to lunch and dinner with friends. Also, yesterday, we filmed TOG. We were live, which we try to do once a week or every other week on Instagram. We just sit around and talk, or ask the audience, "What do you want to know? Ask us anything." Joc, my best friend and I, are more reserved, but the other three will say anything.

Okay. And you go out with friends for meals a lot?

Yes. My favorite place is called La Tablita here in Cathedral City where I live. Then there's Lulu's in downtown Palm Springs. I get their strawberry salad with salmon. That combo scared me at first but Dag! It's really good.

theoldgays
A post shared by @theoldgays

I've only been to Palm Springs a few times. How would you distinguish Cathedral City from Palm Springs?

I'm just five minutes from Palm Springs. We're sister cities and we're both pretty gay. This is a wonderful haven. Yes, we have the enemy out here but they deal with it. I have two friends who got beat up one night, but they were in the wrong because they made fun of someone they passed and he didn't like it. I said to them, "I'm sorry you both got beat up, but you brought it on yourselves. Everyone's going to call this a gay bashing but it wasn't.

Oh, shit. What did they say to him?

I don't remember. One of them got his head busted. But they're both doing amazing now.

Well, that's good, but yeah—don't provoke people. So speaking of "the enemy," I noticed on your personal social media that you are a robust Trump hater.

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A post shared by @jessay.l.martin.12

I have to admit, I'm very unhappy about his win and very worried about what's to come and I certainly will protest what I think is beyond bearable, but I don't have the kind of white-hot outrage I had after his first win. The sad truth is that, whatever you think of it, people—not just white people this time, either, which made it easier the first time to say that his win was racism—wanted him back. And there's a lot in that to unpack, but it's made sheer outrage more difficult. Do you feel that way?

No, because I don't give it that kind of power. The last time Rump won—and yes, I did say Rump—I was sick in bed over it, so this time, I'm not watching. I'm being aware, yes. I watch the news once a day but I'm not spending all day in front of a TV watching something I don't agree with. As a gay Christian man with a dirty mouth, I pray a lot. I give it away and I don't pick it back up. I've finally learned to do that. My body went frigid just hearing you start to talk about him. I choose joy in my life and [stuff about him] doesn't give me any kind of joy.

Yes, I certainly understand that take. So to go back in time a bit—can you paint a picture of your childhood growing up in Tennessee?

Awesomeness most of the time. I didn't realize that we were poor.

A very young Jessay (from TOG Instagram)

That was just the neighborhood. We had running water but not hot water and we burned wood. My mom worked to keep our tummies full and clothes on our back. And when we asked for things, she would somehow get it for us. When we asked her how, she would say, "I'm a mother—we just do that." Now I appreciate it, but if I'd known then [the lengths she went to], I'd have squeezed her to death. I'm a hugger, by the way, a serious hugger, and I will tell you if you are not hugging me right. (Tim: Sadly, Jessay told me he had no childhood or family photos to share.)

What's a good hug?

When you just feel the love oozing in from this other person. I give the best hugs. Don't give me a little pat. It's got to come from deep within my soul.

Okay, I will be sure to give you a really good hug when we meet. So what about your dad? You've talked about him a bit on TOG.

He was the sperm. That's all I can say. My dad and I were so much alike and I learned so— I had to learn that the world wasn't just about Jessay. I had to learn to love him before I could move on in life after he died in 1972, when I was in college. I hated him until two years ago. Because he wasn't there for me—in any way. We lived in the same house, but when he came in, the whole— we went from laughter to quiet.

Here is Jessay talking about his father:

mattcullen
A post shared by @mattcullen

Was he an angry man?

He did not like— I was a sissy, I couldn't help it. I still am! But he didn't like it. But I had fathers, though—men in my life who knew I was a sissy but took me in their arms along with their own sons and taught me stuff.

You mean the fathers of friends?

Yes. As for my own father, I look back and say, "Well, he didn't know [how to show me love]," but that's no excuse. He could've tried.

Wow, this echoes so much thoughts about my own father. I think what I've realized so much since he died in 2017 was that we were basically aliens to each other. You know, he wasn't hostile to me—he basically let me do my thing—but we were from different planets. Neither of us had any interest in what the other was interested in, which for him was sports and for me was arts, books, music, etc. And that has tempered a bit my anger toward him, feeling like he barely ever showed me love or affection, because I guess he showed his love by being a responsible father who showed up for most stuff. But we were not on the same page. Does any of this resonate?

But you were a child. Every child wants to be loved.

That's true. I think a big difference is that straight men today—even conservative ones, MAGA or whatever—they know there's a very good chance their kids could be gay or trans or whatever and so perhaps they're more poised to deal with it. It wasn't like that when you or I were kids. I think we were shocking, off-putting aliens to our fathers.

My mom said to me, "Your dad did his best," and I go, "Uh huh, well his best wasn't good enough. No more excuses."

And what did your mom say to that?

She went, "Okay, baby." She passed away 11 years ago.

Jessay talking about racism in the performing arts…this also includes some photos of younger Jessay (handsome!):

theoldgays
A post shared by @theoldgays

I sense that you miss her a lot.

I miss her more than a lot. I talk to her a lot.

Jessay and his mom (from a TOG Mother’s Day Insta post)

Does she get back to you?

I don't know. But every time I talk to her, I come up with something. I'll tell her I'm having trouble with this or that, and then after I've stepped away from the issue, the answer comes.

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