When Mike Doughty decided to make a video for his new single, “Wait! You’ll Find a Better Way,” he turned to artist Max Skaff. The pair have collaborated before — Skaff also directed the musician’s “I Can’t Believe I Found You in That Town” clip — and Doughty trusts the filmmaker implicitly. “I always just let Max go,” he said. “It’ll be a better video that way — a personal piece of art.”
In fact, Doughty had only two requests for Skaff — that the director craft an open-ended denouement (“I loved the kind of haunting ambiguity of the ending of ‘Can’t Believe,’ and I asked him to steer it that way”) and that the video involve a trans love story.
“Wait! You’ll Find a Better Way” is a black-and-white video detailing a getting-to-know-you date. The lead actress, a transgender woman named Larissa, is shown doing her usual date-night prep, before her beau arrives at her apartment. The two talk, drink and flirt. At the end of the video, Larissa falls asleep, and her date leaves her a note — with unknown contents — before slipping out of the house.
Skaff and Larissa collaborated together directly on the video’s contents, storyline and ending, molding it into something that suited how the latter wanted the video to unfold. “We ended up deciding that we wanted a more positive and ‘cute’ ending because that’s what Larissa’s perfect date looked like to her,” Skaff said. “As a transgender woman, it is often a lot harder for her in the dating and relationship world because she says that a lot of men just want to be with her as some kind of fetish, and then they go on and live their lives as straight men dating cis-women.”
Taking an unscripted, documentary-like approach to the clip was also important to Skaff, a transgender man who started his transition in the last few months. “I feel like trans people are usually portrayed in a false sense on movies or television,” he said. “I think what America thinks a trans person is ‘supposed to look like’ is usually very inaccurate and often offensive. What we need to be educated on is more often than not after medical intervention, a trans person looks exactly like the gender they are medically transitioning to look like. You would never even be able to tell.
“I wanted to avoid making a story of how a transgender person is ‘supposed to be’ or any stereotypes that further separate transgender people from ‘normal people,’” Skaff added.
For Doughty, commissioning this video was also a way to ensure that the song’s message and perception were not misunderstood. Long after he recorded “Wait! You’ll Find a Better Way,” which appears on the 2016 LP “The Heart Watches While the Brain Burns,” House Speaker Paul Ryan launched a political website called “A Better Way.”
Upon seeing the latter site, Doughty felt compelled to reclaim the titular phrase. “The song is about being mired in anxiety and seeking a way out,” he said. “Then somebody showed me the Ryan thing, and I thought, I really, really need not to be associated with that. The endemic transphobia of the Republicans being a big part of my anger.”
Skaff, who records as a rapper under the moniker Uncle Meg, feels similar urgency about taking an artistic stand.
“Especially now more than ever, with a current political situation that is basically hell for anyone who isn’t white and straight, it’s important for us to use as many platforms as we can to educate and normalize what it means to be transgender,” he said, “because, unfortunately, from what we’ve seen in recent news, there’s so much discrimination and a lot more work to be done. And, as artists, this is our job and also our responsibility to educate and advocate for ourselves. It’s our form of resisting the current political and cultural situation.”
Doughty is currently on tour with a backing band featuring his long-time foil Andrew “Scrap” Livingston and members of ’90s rockers Wheatus — a combination that’s led to dynamic, high-energy shows melding his solo work and songs from his former band Soul Coughing.
Meanwhile, Skaff is working on some new music but has mainly been focusing on his personal life. “My transition has been a full time job on its own, so I’ve had to focus a lot of time on my health and well-being,” he said. “I’m getting my name legally changed right now, and I have my surgery in March.”
Skaff is planning to undertake, while he recovers, a donation-based sale centered on stickers created to promote Uncle Meg’s 2016 album “Bug,” with proceeds going to the New York organization Transgender Legal Defense & Education Fund. “We receive a pro bono lawyer to basically guide us through the whole process and get our paperwork and court dates all set for us,” he explained about the fund dedicated to helping trans people change their legal names.
When asked the ways he relates to the song, Skaff singled out a chorus lyric (“Wait! Oh, you’ll find a better way”) and then added a personal anecdote: “I can only speak for myself, but when you are going through a deep internal crisis your whole life, it can be super easy to end up in a dark place,” he said. “I constantly asked myself my whole life, before I transitioned, ‘What the fuck is wrong with me?”
Added Skaff: “I never asked myself that question again after I got my first T shot, that’s how right it felt. It was as if my body just soaked it all up, like it needed it its entire life. Sometimes I even wondered if I would make it to 40, or if I would just kill myself before then, because I was so uncomfortable. Not to be so dark! But this is a real life or death matter for most of us. So I do believe I found a much better and happier way to live my life, even though the waiting really sucked.”