Funny People (2009)
Death is one of those topics that is really best explored with humor (or a shitload of gore, but that’s for a different list entirely). While Funny People doesn’t necessarily stand out as writer/director Judd Apatow’s greatest piece of work, Sandler’s performance as a dying man struggling to find humor and meaning in his situation does. It’s here that Sandler surprisingly does his best work: somewhere between irreverence and thoughtfulness.