Late Night just felt a bit paint by numbers, and a bit wish fulfilment. It gives us a phenomenally emotional scene between two brilliant actors in the moment when Emma Thompson and John Lithgow decide to move past her affair, and there are the occasional laugh-out-loud moments, but the rest is fairly vanilla. None of the characters are bad, but few are particularly more than one-dimensional. Apart from Thompson, no one really gets any character development (and even with her, it's a rollercoaster of likeable, bitch, barely empathetic so... not sure it's forward development); I guess you could argue that Mindy Kaling's Molly grows in her self confidence, but she comes into the film overly confident, gets lucky break after lucky break, and never really gets slapped down enough for it to feel like a genuine arc. Stuff just kind of happens.
It feels like they had a good idea and no surrounding plot. As a result, it's never entirely clear what story the film is trying to tell. Are we meant to focus on the in-your-face messages about Kaling's race and sex being used against her? Sure, the film makes a point of highlighting both overt racism and the subtle microaggressions that create a toxic environment, but Molly as a character isn't someone who is being held down by the system. She is rightfully being judged as an amateur and only gets the job because of a pointless sequence of plot events. They could have made her a genuine breakout standup, someone who has been in and out of the business for years, going for a long-shot job, but no. She's a nobody without any valid reason to have talent that just gets lucky.
Or Thompson's character, whose story about losing her late-night talk show is at least novel and interesting, but paired with a character who has no real purpose. A big thing is made of her being sexist at the start of the film, but that never transpires (if anything, it feels like they felt the gender card was easier to play than the race one as an excuse for Molly to be hired). She's completely out of touch, yet seems totally okay with modern slang and tech terms. And she might be on a redemption arc, but she never really gets redeemed. Bad things happen, she overcomes, everyone goes back to where they were at the start. The sleazy coworker is still sleazy; the sexist coworker is still sexist; the boringly attractive "nice guy" coworker is possibly now Molly's boyfriend (more wish fulfilment? Could she not have just been successful at her job, she has to get a guy too).
But worst of all, for a movie about late-night comedy, starring a cast of characters who are all supposed to be comic writers or stand-ups, and with a genuinely funny lead writer in Kaling, the dialogue is just flat. They needed Marvelous Ms Maizel moments of utter, side-splitting joy and hilarity. We get one heartfelt, well-written apology speech and nearly two hours of mediocre, sitcom gags. Even the jokes that get Molly's character elevated up the ranks are decent SNL punchlines at best. And yeah, that's kind of late-night shows in a nutshell, but that format works because of the connectivity and the famous guests. It doesn't work as a story-driven film.