Tomorrow’s Too Late is a documentary that will become vital viewing for not only young transgender people, but those who want to learn about transitioning. Dyan Holloway’s story is truly inspirational in Terry Loane’s remarkable film.

Musician Dylan Holloway, formerly known as Lots Holloway, stepped away from the spotlight during the 2020 lockdown to begin his gender transition. Once a rising star as a teenager on the UK’s X-Factor and then as a solo artist, Dylan now faces a profound personal and professional crossroad.

The importance of documentaries or any media that give an authentic look at the transitioning experience has never been higher. Tomorrow’s Too Late is the perfect film for those in the midst of their own journey, family and friends of those people, and those just wanting to know more about it.

Being trans is not a simple thing for one to experience or understand, and seeing an experience like Dylan’s is so necessary. At the same time, there is clear pain and struggles in his journey, the sheer positivity that blasts through the screen at you as we watch on is staggering. We see Dylan move from someone insecure with themselves to this beaming light of a human. Finally able to feel and sound like who they were meant to.

Filmed during lockdown, Loane could easily move out of the diary entries that Dylan has been logging during that period, but wisely decides to keep them as we get further glimpses and thoughts into what Dylan has been experiencing. By doing this, we can feel as close as possible to him, and damn if that connection isn’t an emotional one.

It’s impossible not to feel a deep connection to Dylan throughout the mere 63 minutes we share with him. Even if you are not a person who struggles with their gender identity, you relate to him. He is a person who just wants to be free and be the person he always thought he should be. We all have that want in some form, so to see his struggle and unpack all of that pent-up emotion is incredibly poignant.

Tomorrow’s Too Late covers some of the typical topics you’d expect in a documentary about a person transitioning, from Dylan’s reflections on his childhood and the distance he felt from his gender to his family and friends’ perspectives. These could easily be presented in a stereotypical manner, but Terry Loane’s direction infuses them with a personal touch, making the film feel remarkably authentic.

Coupled with Dylan’s transition story, a major quandary arises for him. The hormone therapy he requires could do irreparable damage to Dylan’s singing voice. The very thing that has kept him through the worst of times is one of the main ways in which he earns a living, as well as being that core emotional and mental outlet for his creativity. That could all disappear in a matter of months.

Several moments in this part of Tomorrow’s Too Late truly grab you. Seeing the emotional struggle Dylan goes through as he documents this part of his journey is heartwrenching. We are so happy to see him become more confident in himself as his appearance changes, but he is riddled with doubt about his singing voice.

The songs he once had the ability to sing off the cuff at a piano are now gone, vanished, mere cracked whispers in the wind. It’s devastating to watch as he adapts and tries to figure out how to get to the light at the end of the tunnel with it. Rather wonderfully, the monthly check-ins allow for something beautifully creative to come to the fore. This moment makes the entire worth watching on its own.

Despite the positive outlook that Holloway and Loane convey throughout Tomorrow’s Too Late, there is a lot of pain here, and it becomes one of the film’s other strengths. There is no sugar coating the transitioning process into a wholly positive experience. A person’s body is changing in dramatic ways and at times rapidly, which is a massive thing to manage psychologically. Holloways lets us into that struggle and the sacrifices in such a refreshingly open way.

Luckily for us, that isn’t the only reason to watch Tomorrow’s Too Late; there are countless. Terry Loane has made an immensely intimate film that is as affecting as it is powerful. Dylan Holloway shows everyone that while finding the real authentic you may take a long time and may have some serious risks, that it is still worth doing. Your happiness is paramount, and if you have a strong support group like Dylan has, then that journey will be nothing in comparison to the reward of being the real you.

★★★★ 1/2

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