Left: Serrato... Right: Heaven
I Thought You Knew perpetrates the trope of trans women "tricking men" and how many of the men linking up with them have no idea the women they're attracted to have a trans past. In reality, the vast majority of men who have perpetrated violence against trans women knew very well who they were involved with and even sought out those women specifically for a sexual connection with a trans woman. He writes (as Heaven), "It's pretty much autobiographical, It's real sad. But don't worry my babies, I'm all good now, I gotta a real big vibrator.") In other words, men breaking up with trans women is a big joke, not a situation which is rife with abuse both emotional and physical as well as violence and even murder. In the real world, Serrato is a gay man who doesn't in any way actually live even part time as a transgender person. It's a schtick.
Previously, Serrato had another video called "Heaven" about his trans character transitioning and hooking to save up for "her fishy" (aka vagina). It's all done with a lot of ghetto patois even though Serrato makes no direct attempt to "black up." It has lots of jokes about "lady bits," giving oral sex, trans-related surgery and how she's going to be a lady rapper when she gets a pussy. There don't seem to be any actual trans women in the video which goes a long way to make trans sexworkers lives into a joke. The term "tranny" is repeated ad nauseum, at one point Serrato saying "look bitch, I'm a tranny... t.r.a.n.n.y."
While Serrato is a comedian first and there's little question the videos are not made as serious social statements about the lives of trans sexworkers, it's also true that he falls into a category of "gay-themed" entertainment which laughs at the supposed trashiness and marginality of trans women involved in the street economy. Moreover, this genre of humor seems to overwhelmingly be done by white, non-trans performers for overwhelmingly white, non-trans audiences willing to laugh at the hi-jinx of trans women of color. Note that in "I Thought You Knew" the boyfriend being referenced is clearly supposed to be a black man and, at one point, there are what sounds like white men trying to imitate the voices of black trans women. It is a kind of aural blackface, albeit without the greasepaint.
Left: Serrato... Right: a real gay man
Why a rather preppy gay man feels he can only get big laughs when dressed as a take-off of a trans hooker is a question which needs to be asked. Is his own life too flat and colorless to be the source of the outrageous humor he's trying to express and market? Why do so many gay performers feel the need to objectify and even ridicule trans women to live out their own transgressive dreams? How is it non-trans men feel they possess the entitlement to make highly personal and even dismissive observations about trans women's bodies, transitional struggles and life experience? I'm aware chubby gay men can feel marginalized and unappreciated in their own communities, but why is this an invitation to make complex and difficult trans lives into cartoons?
Serrato and gay buds explaining the realities
of tranny hookerdom.
In none of the performances of this genre have I ever seen an expressed appreciation for what trans women, especially those from low-income communities of color, actually go through nor, the very real danger those women are exposed to as the group with the highest seropositivity rates, horrific rates of rape and domestic violence and the worst murder rate of any group. No, that's not the stuff of laughs, but it might give a depth of portrayal and empathy to what is now little more than crass minstrelsy and lazy cultural appropriation.