What I concluded after 20 years wondering whether William Shatner’s ‘That’s Me Trying’ is serious or not

Back in 2004, William Shatner finally tackled the fabled tricky second record with Has Been. He’d been mulling over his sophomore effort for 36 years—pondering how best to follow up 1968’s The Transformed Man, a record described by many as the album that Sgt. Peppers could have been. If the ‘Fab Four’ lifted music to new heights, then Shatner beamed it up beyond the stratosphere with his musical monologues of William Shakespeare, Edmond Rostand and some guy called Frank Davenport. 

Topping an effort like that is like a mountaineer wondering what to do next after dragging a piano up to the peak of Everest. Proverbial mountaineer and Shatner alike had only one option: bringing things back down to Earth. With Has Been, Shatner mixes pop covers with a string of original songs portraying him as a man so washed up that a whale carcass looks like it’s practically still riding the waves by contrast. The zenith of this fall from grace fable comes with Shatner’s opus, ‘That’s Me Trying’.

For those who don’t know it or want a recap of the absurdity for old time’s sake: the song is essentially the tale of an absent father reaching out to a daughter who, it turns out, has been living “two miles away for the best part of 20 years”, all set to the same melody as Robbie Williams’ ‘She’s The One’. It is a song that breaks your heart and puts it back together again. It makes you smile like a nun cycling down a cobbled street, and makes you sad, like a nun cycling along a cobbled street—offering joy and the question of whether you should be enjoying it in equal measure.

This puzzlement is the crux of the song. Practically since its release, I have been wrestling with its impenetrable brilliance, looking for a chink in its earnest surface to see whether there is a joke beneath the ballad that Bernie Taupin (probably) wishes he wrote. It is an unreliable stream of consciousness that should reside in the Louvre, and I have no doubt that in years to come a procession of scholars will marvel at its grace, trying to grasp its magnitude like first-year politics students ogling at Lenin lying in state in the Kremlin. 

Crafted alongside Ben Folds and Aimee Mann, the song begins with Shatner reeling off the premise of a father rekindling his relationship with his daughter. At this stage, the only postmodernist flourish is keeping digressions like “You were born in June or was it May?” within the song itself. A lesser songwriter might have cleared that up, but Shatner just hands it over to Folds and Mann to rattle off a singalong chorus. 

This is how the song progresses for the most part, but with growing frequency, Shatner suddenly begins littering the track with absurdities. The premise of the father pitching that they both read a novel (not a thriller) before they meet so that they can talk about that rather than “that bad stuff” is quirky enough, but he laces this peculiar specificity with casual wild remarks like “I don’t want to know if I’ve got grandchildren” and “I don’t want to know what happened in your thirties.”

These strange remarks weave a snare that I fell into two decades ago and in the intervening years, I have had no success escaping, mostly because of my lack of desire to do so. I like the mystery of lines like “Do you still see your sister Lemli? Bring her too…” Surely, Lemli would also be his daughter – the stern invite bolsters this assumption – but we are left none the wiser as to why she merely seems to be an afterthought. Are we dealing with a father so neglectful that in trying to reconcile one relationship, he has almost forgotten about the existence of another? Is that the message?

We will never know. And I, for one, don’t want to. Sure, I could probably reach out to Ben Folds through PR contacts and have this mystery solved, but that, to me, would be like the History Channel finally figuring out conclusively how the pyramids were built. This evergreen mystery has provided my humble conclusion after years of laughing along to ‘That’s Me Trying’: some jokes should never be killed.

Shatner’s joke is comedy at its finest. He knows where he stands in this whole thing, but we don’t; he is the categorical jester. As a man and comic, he defines the power of wonder, not just through this song but in everything he has ever done. He is the spaceman who actually travelled into the stars… as a 90-year-old man alongside the billionaire book salesman Jeff Bezos. He is the star who transcended the role of the fantasy rocket man and became a pioneer of space travel in his twilight years. He is the father desperately appealing for retribution wholly hamstringing his effort by steadfastly insisting that there is no mention of any potential grandchildren for reasons unknown. He is a marvel in every which way, and ‘That’s Me Trying’ is his delightful, inexplicably past-tense, masterpiece. 

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