Watch Sean Penn's Bizarre Appearance On The Late Show With Stephen Colbert

One of the most consistently vocal entities within Hollywood, Sean Penn generally attracts a lot of attention for his public appearances. His recent trip to The Late Show with Stephen Colbert could not have been more bizarre, either, thanks to the actor's mental facilities still being muddied by the prescription sleep aid Ambien. As opposed to being a loud and bawdy interview, Colbert's chat with Penn was the kind of surprisingly frank and eye-opening conversation that doesn't come to late night all that often. (Smoking was involved, too.) Check out part of the interview below, especially how bemused Colbert is.

Promoting his new book Bob Honey Who Just Do Stuff, Sean Penn already made headlines this week for a CBS Sunday Morning interview in which he spoke out about wanting to quit acting due to a growing disinterest in that side of his career. And to be expected, that subject was broached fairly quickly, though not before Penn admitted that he was still feeling the effects of an Ambien he'd taken to fall asleep after a red eye flight the previous night. And it's a VERY good thing that admission came up so early, because it was necessary to understand why the interview coasted along in such a strangely hypnotic fashion. It also explains why Penn suddenly felt fine to light up a cigarette on stage, as if that was still the late night norm.

The conversation itself did feature some loose-end hiccups here and there, particularly after Stephen Colbert made his Netflix jab, but for the most part, Sean Penn made it fairly clear that he shifted interests from acting to writing because he doesn't want to continue dealing with Hollywood bureaucracy, with middle men micromanaging everything. From a creative standpoint, he said that while some collaborations can be wonderful, that's not always the case, and his views were succinctly whittled down into this claim: "I was never disappointed with me." When one doesn't want to work with anyone else, it definitely helps to be comfortable with oneself, especially when Ambien is involved.

The interview really took a trippy detour when Stephen Colbert started asking Sean Penn about Bob Honey, which first came to life in 2016 as an audiobook that also featured narration from Frances McDormand. Penn shared that the project's earlier conceit -- involving a country-crossing journalist named Pappy Pariah -- was basically hogwash, and his explanation for how he crafted the material is the stuff of mushroom trips. I'm kind of into the idea of a late night talk show starting up where all the guests have to take Ambien before appearing. Wait, no, that actually sounds like a waking nightmare.

Before saying goodbye to thespian duties, Sean Penn will next be seen on the big screen in Farhad Safinia's drama The Professor and the Madman. The two-time Oscar winner is also set to lead his very first TV show with Hulu's upcoming space drama The First, which was created by House of Cards' Beau Willimon.

With other fairly unpredictable guests on the way, The Late Show with Stephen Colbert airs weeknights on CBS at 11:35 p.m. ET. To see what other new and returning shows are hitting primetime soon, head to our midseason premiere schedule.

Nick Venable
Assistant Managing Editor

Nick is a Cajun Country native, and is often asked why he doesn't sound like that's the case. His love for his wife and daughters is almost equaled by his love of gasp-for-breath laughter and gasp-for-breath horror. A lifetime spent in the vicinity of a television screen led to his current dream job, as well as his knowledge of too many TV themes and ad jingles.