Conan O’Brien Announces His Possibly Villainous ‘Toy Story 5’ Role With Insane Video

Watching Toy Story 3 was the first time my dad and I cried together (and one of only a few times I’ve seen him cry). I was in my early 30s, he was in his mid-60s, and my niece, who was watching it with us, was eight (she didn’t shed a tear). Watching the toys we’d grown to love collectively accept death while approaching a raging furnace was sad enough. Seeing Andy give up his childhood while passing it on to a new kid? It was devastating for me, as someone who was learning to grow, and my father, who had taken young me to see the first film over twenty years earlier. It felt like a fitting end to a great franchise.

Then, I was like, “Hold up, they’re making a fourth one?!”

And they did! And it wasn’t that bad! While Toy Story 3 hit me at the exact right age, I ironically thought I was too young for the fourth installment. It felt like a meditation on age and retirement, about finding your purpose after children. I haven’t seen it since it arrived in theaters, and I genuinely wonder if it would f*** me up even more now that I have kids. I could also be misremembering the themes, as I haven’t seen it in six years. But it felt like a fitting end, as it split up Woody and Buzz, the duo who started the whole adventure.

Then, I was like, “Hold up, they’re making a fifth one?!”

They are! Toy Story 5 is due to be released on June 19th, 2026 (arriving just in time for the current administration to claim celebrating Juneteenth is a federal crime). Pixar’s description of the upcoming sequel is as follows. “The toys are back in Disney and Pixar’s Toy Story 5, and this time around, it’s Toy meets Tech. Buzz, Woody, Jessie, and the rest of the gang’s jobs get exponentially harder when they go head to head with this all new threat to playtime.” Huh! I don’t understand how Woody will be involved given the events of the last film, but Tom Hanks has been confirmed to return, as has Tim Allen, so it’s happening!

In addition to returning cast members, new voices will be joining the fray. Among them is legendary talk-show host and greatest Hot Ones guest ever, Conan O’Brien. The red-headed wonder will be playing the character of Smarty Pants, which he announced via Instagram in an insane video. His hair looks crazier than usual (by his own admission), he jokes about wanting to voice Woody or Buzz, and he laughs maniacally into the camera while turning his face beet red.

The whole thing is very exciting, especially if you start putting some pieces together. The name Smarty Pants certainly sounds like something you’d call a high-tech toy. Since Pixar is saying the toys will go head to head with some tech, could O’Brien be the antagonist of the film? Will he join the ranks of Sid, Lotso, and Stinky Pete? We’ll have to wait a bit to find out, but if they are announcing his role this far in advance, that’s where my money’s at.

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