Alternative Character Interpretation: Caden is gay and in severe denial. It's even occasionally alluded to In-Universe, such as several characters asking if he is, his dying daughter insisting he left her to be with a man named Eric (implying he may be repressing actual events), and all but one of his shown sexual encounters end either due to him ending it or due to interruption. Even when Tammy asks if he is gay, Caden responds "I only love women"note Which could arguably be interpreted as "I'm not attracted to women, but I only love women", and the time when he has sex with Hazel a second time can be explained as a singular exception.
Caden has sex with several women throughout the film, several times, and the sex only ends prematurely twice, once because he starts crying, and once because he gets a call saying his father is dead.
Harsher in Hindsight: In the opening of the film Caden reads a newspaper article and thinks Harold Pinter's died, then reads it again and notices he's actually won a nobel prize. This is a reference to a flub made by the reader on Sky News. Pinter then died for real less than two months after the film opened.
And also, it is now really hard to watch Caden's death at the end without thinking about the death of Philip Seymour Hoffman.
Jerkass Woobie: Caden is not particularly likeable, being a solipsistic, morbid, arrogant character. And yet despite his unlikeability, the audience can't help but feel some measure of sympathy for the misery that is his life.
Tear Jerker: The bedside goodbye to a dying character, doubles as Funny Moment, simply because the ludicrous amounts of schadenfreude that Kaufman throws at Caden.
Millicent's monologue about the daughter she promised her mother she'd have, but never did.
Caden's distraught reaction to seeing his daughter having become a tattooed erotic dancer.
Olive reminiscing on playing the fairy game with her father.
Caden and Hazel's last night together, especially when you know what happens next