When I was growing up in the 90s and 00s, the late-night comedy landscape was bleak to say the least. Old, creepy and painfully unfunny figures like David Letterman and Jay Leno reigned supreme. Conan O’Brien was a breath of fresh air when he unexpectedly replaced Letterman in 1993. His show’s patented brand of surreal, anxious and, most importantly, self-deprecating humor resonated deeply with my generational cohort: you know, the anxious, ungrateful brats rattled by 9/11 and then the Great Recession. 30 years later, however, the shine has finally come off the apple. In his most recent project, the travel show Conan O’Brien Must Go, the comedian signals his growing obsolescence and suggests that his time may have finally passed.

One reason Conan O’Brien Must Go stinks of irrelevance is simply because it brings nothing stylistically new to the table. In terms of its structure and tone, the show replicates what Conan has already done before with Late Night and TBS’s Conan. The program particularly feels like a retread of the latter. During his tenure on basic cable, Conan produced a series of travel specials entitled Conan Without Borders. Many segments from those specials show up once more in Conan O’Brien Must Go. There is the self-deprecating humor. The awkward “man on the street” interviews. Several scenes feature the comedian being an intentional and (mostly) good-natured creep around ladies. Conan also basically replicates verbatim select Without Borders‘ bits: such as recording a song with a local band and shooting a regional TV show cameo. One of the best Without Borders sequences was undoubtedly when Conan practiced Australian slang in Sydney, and even this occurs again here. The only difference being it takes place in Ireland this time around and is considerably less funny.

Conan O’Brien Must Go‘s problems go beyond being a mere rehash of previous material. Now 61, the Conan who shows up in Must Go feels, perhaps for the first time in his career, like a man out of step with the culture. Without Borders ceased production in 2019, and the world has changed dramatically since then. Power and wealth inequalities have grown progressively more obvious and disgusting, as has United States’ horrifying conduct around the world. All of these factors compound to make select Must Go bits particularly difficult to sit through.

In the show’s Norway episode, for example, Conan meets a fan and tours his apartment, picking apart mildly embarrassing aspects like recently expired food. Later, he forces two feuding Norwegian fishermen to reconcile while BOMBARDING them with comedic schtick that obviously doesn’t jive with their cultural sensibilities. While these sequences may have felt harmless even a few years ago, they now come across as tone deaf. It’s frankly jarring to see an insanely wealthy and powerful entertainer (with an immoral net-worth of $200 million) “joking” about the living circumstances of a normie. Similarly, it is uncomfortable to watch an American elite gallivant around the world seemingly oblivious to the mores and preferences of those whose country he is visiting.

Must Go also suggests Conan is now become too insulated, too surrounded by yes men, and too flush with cash to apply the necessary scrutiny to make lean and effective comedy. HBO clearly spent a fortune on Must Go. I would even bet my retirement account that they dangled full creative control as an incentive for Conan to sign on. The star clearly took those resources to go hog wild with his most elaborate fantasies, which are by far some of the program’s worst segments.

In each episode, the show breaks from its documentary style for short, dramatically staged sequences. For example, in Norway, he dresses up like a Viking. In Thailand, he comedically “fights” and “beats up” a team of elite Muay Thai fighters. And in Ireland, he engages in a pretty terrible parody of The Lighthouse. Aside from being bad, these vignettes prove that, quite often, great art comes from adversity. Despite having far more resources during his career than almost any comedian alive, Conan’s earlier remote episodes still often felt rather small, scrappy and innovative. He was forced to call on his considerable wits more than rely on his bank account. By contrast, the non-documentary scenes in Must Go suggest that Conan is following in the footsteps of other artists who became less effective, judicious and thoughtful the richer and more powerful they became. These are folks we all know and used to love. I can most easily think of Hollyweird types like Tim Burton, Quentin Tarantino, James Cameron, Michael Mann, Peter Jackson and, of course, George Lucas.

I wanted to enjoy Conan O’Brien Must Go as much as anyone else. Like so many of people of my generation, I grew up watching the man. I would even credit his style and vibe are probably foundational to my own sense of humor. Yet the fact remains that Conan has been doing his schtick for as long as I have been alive. After three talk shows, a comedy tour, a documentary, a podcast and now a travel show, it’s only natural that he has become a bit long in the tooth. That decay is abundantly clear in Must Go, both stylistically and due to Conan being now older, richer and having fewer barriers pushing him to deliver lean, innovative and high-quality comedy. “Time waits for no man,” or so they say. And in Conan O’Brien Must Go, it seems like it has finally come for the titular comedian.