Howard (Will Smith) was a once dynamic creative executive, who let his company on charisma and talent. But now he is a broken, shell of a man after the death of his young daughter. The tragedy broke up his marriage and he is alone literally and figuratively in his grief, unable to come out of his hole. His longtime business associates Whit (Edward Norton), Clair (Kate Winslet), and Simon (Michael Peña) are sympathetic, of course, but they are tapping their watches as it has been a couple years. Howard won't sign off on his power over the company while he is emotionally incapacitated, and their business is starting to spiral.
So what does a family-like group of co-workers do? Well, why not put their friend in situations that will make him look at feel like he has lost his mind, so a professional can come evaluate him and remove him of power. Yeah, that's kind of a dick move.
The buddies hire some local actors to represent Death, Love, and Time (Helen Mirren, Keira Knightley, and Jacob Latimore, respectively). Howard has been secretly writing letters to them and dropping them in mailboxes, which the friends have very illegally intercepted—Howard's colleagues think that it is a great idea to hire the thesps stretch their skills, show up in Howard's life manifested as people on the street, and offer him sage advice in response to his letters. The friends will secretly film these meetings and remove the actors, making Howard look crazy. See? Proof. (Insert deadpan emoji here.)
The thing is, the superb cast (I mean look at the list), almost pulls it off. Simon (Peña, particularly good) confesses to Mirren's Death that his cancer has returned. Whit, who is an absent father, flirts with Knightley's Love and tries to makes sense of why he has been such a douche to his family. And Clair, in the most ham-handed subplot, is vexing about her biological clock so of course confesses to Time her regrets about putting job before family. Howard starts to go to a support group led by a lovely woman named Madeline (Naomie Harris), and yes, some scenes may wring some tears.
If the build up toward the yucky corporate confrontation doesn't make you feel kind of awful, the filmmakers throw in a twist that is supposed to make you feel better. I didn't hate it, but I've heard that some audiences completely revolted at the end. While watching, you can't really get past that the central premise of the whole thing. Rather than making you feel good, it makes you actually feel more yucky about humanity.
The only extra is A Modern Fable: Discovering Collateral Beauty, where the actors, director, and screenwriter/producer talk about the film.