Hello, Goodbye: Stephen Colbert and the endings we never imagined

A row of walk-up apartments at the junction of Upper Serangoon Road and Lorong Lew Lian. Singapore, 2015. (PHOTO: Laremy Lee)

It wasn’t supposed to end like this.

The Late Show with Stephen Colbert (LSSC) was supposed to be the final stop on the comedian and talk show host’s long and illustrious career, or so I always thought.

He would live out the rest of his working days behind his iconic desk inside the Ed Sullivan Theatre, where David Letterman once sat and where The Beatles once played before a screaming audience in a performance that changed the course of history.

He would have spent the next dozen years or so doing what he had spent decades perfecting: making self-deprecating jokes and wisecracks about public figures while interviewing film stars, presidents and musicians with equal ease, night after night.

And when it was time, he would have graciously passed the baton to a deserving successor – Trevor Noah or Ronny Chieng, perhaps – before riding off into the sunset, after being feted for his contributions to both comedy and public discourse.

But that assumes the world functions according to a rational narrative structure.

By this logic, if you are a good person and do good by leaving the world slightly better than you found it, you’d eventually get the happy ending you deserve.

Why, then, do bad things happen to good people? I don’t have an answer to that question.

The only thing I am sure of is this: things will happen to people.

***

I am very familiar with how things aren’t supposed to end.

A small part of me believes the theory about how some cataclysmic event occurred in 2016, rupturing our original timeline and creating an alternate reality.

Another part of me also believes in the meme that all of us died in 2020 when Covid-19 happened and this is the hell we have been consigned to for the rest of eternity.

In my heart of hearts, however, I know neither of these to be the case.

To believe so would be to shrug off responsibility for what happened with P and me, and to do so would be irresponsible of me.

It would mean believing my behaviour to be an inevitability of fate instead of what it actually was: failure.

I didn’t know how to manage the toxicity of my previous workplace. Neither did I know how to protect myself before it consumed me. I could not stop myself from taking it out, emotionally and verbally, on P. And I had absolutely no idea how to salvage what happened with us afterwards.

In Colbert’s last LSSC interview with his friend and former colleague Jon Stewart, the latter shared a piece of advice he received when Stewart’s MTV talk show was cancelled in 1995. 

“[Letterman] said to me something very profound. He said, ‘Don’t confuse cancellation with failure.‘ …then he said, ‘But in this case, it is also a failure,‘” Stewart quipped.

There is nothing inherently shameful about failing. The shame lies in refusing to acknowledge or learn from it altogether.

***

LSSC began airing in 2015, around the same period I entered what was the most psychologically and emotionally exhausting chapter of my working life.

I was already a regular viewer of The Daily Show (TDS) and The Colbert Report, during the period in which satire in Singapore and the world became a crucial medium in holding power to account.

A quick aside: my mobile phone ringtone is still “Humanism” by Jon Batiste and Stay Human, the LSSC theme song performed by the show’s original in-house band.


Before that, it was “Dog on Fire” by They Might Be Giants, the TDS theme song from 2000-2015.

During those tumultuous years, I looked forward to the small moments when I could decompress with the show, given the ludicrousness of every work day.

It helped me through that difficult period, which also included what was going on elsewhere in the world.

When the US decided to elect Donald Trump as president in 2016, a fresh violation of common sense emerged every day thereafter, courtesy of the chaos brought about by the Trump administration.

Colbert, along with the other late-night talk show hosts, became translators for the absurdities of US politics and the decline the country seemed to be drifting towards.

Much like Cassandra in Greek mythology, however, nobody listens until it is far too late. And by then, there might be no one left to speak.

*** 

In discussions about the arts and media in Singapore, a darkly humorous joke goes like this: Censorship is a badge of honour you wear to show you’ve made your mark as a public figure.

In its own perverse way, censorship is an acknowledgment of power. Nobody bothers muzzling work that says nothing.

There is, of course, some nuance here.

Not every rejection is a silencing. Sometimes, what is being spoken is simply not as precise as it needs to be.

At other times, the truth can be a matter of kairos – though there will always be divergence in views as to when the right time really is for something to be said or done.

It is easy, in moments of discomfort, to frame resistance as persecution rather than sit with the more difficult possibility that the world is responding exactly as it should to something that should not be said or done.

And it will always be easier to reach too quickly for the censor’s knife.

***

Was Colbert’s cancellation a result of failure? 

In show business, some metrics to measure success include viewership, revenue and reach, among others.

By those standards, LSSC succeeded emphatically.

It was one of the most-watched late-night programmes in the US during one of the most politically volatile periods in the country’s modern history.

For all its irreverence, LSSC was serious about philanthropy, raising millions of dollars for charitable causes including World Central Kitchen’s humanitarian relief efforts.

Colbert’s work also travelled far beyond television itself, circulating online as nightly summaries of the bedlam unfolding across the US.

But comedy succeeds only when there exists a shared understanding of reality being transgressed.

And society only functions when institutions remain tethered to the truth and committed to doing what is right and fair.

Once the world becomes unmoored from these bearings, comedy loses its leverage; the absurd ceases to be a deviation from normalcy, instead becoming the norm.

Given the increasingly unstable social and political spheres within the US, it is cold comfort to consider Colbert’s censorship as a badge of honour for his service to a nation on the verge of disintegration.

***

In the final bit on LSSC’s series finale, Colbert comes face to face with an interdimensional wormhole that threatens to destroy the late-night television industry in the US.

On a personal level, the wormhole symbolises the void left behind by the end of LSSC, as well as Colbert’s feelings of dread in having to face an unknown future.

Colbert subsequently has an interaction with Stewart where the latter emphasises to the former that the wormhole is a metaphor for the unavoidable darkness of a massive life change.

Nevertheless, Stewart reiterates, “The only choice you have now is how you choose to walk through it.

“You can go kicking and screaming. Or you can do what you’ve done for the past 30 years when faced with something dark. You stare it down and you can laugh.”

“I’m sorry, Jon,” Colbert replies in a deadpan tone, shaking his head. “I just can’t think of any jokes to say about my giant, gaping hole.”

***

I have a giant, gaping hole of my own. I am still grappling with the grief of losing P. I worry I may never find a love like ours again.

I had always imagined P and I living out the rest of our lives together in tender and comfortable companionship.

We would have grown older together, settling into the rhythms of a long and loving marriage: texting each other memes during mundane Monday morning meetings; heartfelt conversations about literature and life while side by side in bed at night; weekend explorations of parts of Singapore we seldom saw.

We would have spent decades building a shared space filled with laughter and memories of silly moments and books and trinkets from our travels around the world.

And when the time eventually came for one of us to say goodbye – as it must for every couple fortunate enough to age in place together – the other would have smiled through tears and said, “Go,” for we would have already spent a lifetime loving each other.

La tristesse durera toujours; the sadness endures forever. Vincent van Gogh (and the Manic Street Preachers) knew this well enough.

Things will happen to people, regardless of whether we want them to or not. In some instances, they can be avoided. In others, hindsight is always 20/20.

***

As the bit concludes, Colbert reaches an epiphany of his own.

“I think I get it now,” Colbert says, with a look of resolution. “It looks like the end and I wish it wasn’t – but that’s not for me to decide.

“All we have to decide is what to do with the time that is given us,” Colbert intones with equanimity, in a poignant allusion by the JRR Tolkien enthusiast to The Fellowship of the Ring.

Despite all that has happened, I’ve never stopped believing there is still a place in this world for good.

We still have to keep trying to be good people and we still have to keep doing good, by leaving the world slightly better than we found it.

The alternative is surrendering to a culture that increasingly rewards cruelty and cynicism, thereby becoming the very thing that makes the world a worse place to live in.

Thank you, Stephen, for all the wisdom and joy. May this moment be but a pit stop along the way.

When the man behind Dilbert lost his voice

I loved Dilbert when I was younger and used to read Scott Adams’ blog regularly back in the day.

His dry humour and sharp insights into both corporate and modern life was perceptive in highlighting absurdities and dysfunctions which people accepted as the norm back then.

And who has not met someone who completely exemplifies the Dilbert principle? 😂

At some point, however, I had to actively disengage from his material as he moved into increasingly divisive territory.

That shift and decline was striking to me; it seemed to take place around the same time he opened up about his longstanding struggle with spasmodic dysphonia, a voice disorder that affected his ability to speak publicly.

It’s the same condition which present US Health Secretary Robert F Kennedy Jr has discussed living with.

Coincidentally, Kennedy himself is also known for a number of widely disputed views.

I don’t know whether there’s any connection between the health struggles both went through and their later public positions, and I certainly don’t mean to suggest a causal link.

Nevertheless, it’s hard not to notice how different the later chapters of their life felt from their early ones, both before and after being afflicted with the condition.

I wonder whether their paths reflect a familiar pattern among many men who encounter a major personal challenge.

Perhaps they sought support from their network but when that help was not forthcoming, the resulting isolation led them to turn elsewhere and in a completely different direction.

I hope in his next comic strip or podcast, wherever he is, Adams reclaims the kinder, gentler voice that once shone through his cartoons.

May the afterlife be more lovely and less painful than the world he spent a lifetime lampooning.

Before “I do”: Pre-marital literacy and the skills for lasting love

When Bianca Tham, Residential Student Life Manager at NUS College, reached out to discuss a fireside chat with students on how we prepare for love before marriage even enters the picture, I welcomed the opportunity.

We spend years learning how to write essays and build careers, yet almost no time learning how to love well.

As our conversation unfolded, it became clear marital literacy might be a little early for undergraduates.

But pre-marital literacy – the knowledge, skills and attitudes we need before committing to a long-term partnership – is something many of us are already navigating, whether we realise it or not.

Please join me for this event, where I’ll reflect on my own lived experience and invite an open, honest conversation about how emotional awareness, personal values and self-care shape us and our relationships before we factor in plans for marriage.

Whether you’re single, dating, undecided or simply curious, this session aims to help us make more informed and resilient choices in love.

Before “I do”: Pre-marital literacy and the skills for lasting love
Date: Thursday, 29 January 2026
Time: 8.00-9.30pm
Venue: Cendana Master’s Commons, NUS College

Please register at https://bit.ly/NUSCpml

NUS College students: Please sign up early; spaces are limited to 20 pax.
Alum of USP (including the CCP and TDP) and Yale-NUS College: You’re warmly welcome to register too. Alum slots will be released once student places are filled.

Looking forward to a thoughtful evening of conversation, reflection and learning together.