Turns out that the Alexander Payne-Paul Giamatti duo has always hit different, even twenty years before The Holdovers.
A very simple plot but effective as fuck, because the characters feel super genuine. It made it very entertaining.
It's also a great way of showcasing some deeper psychological themes, thanks to the great performances of two self-esteem deficient characters, one being cynical/overthinker and the other one lying to himself about his commitment issues.
The way Payne consistently adjusts its direction according to the drunkness level of the main characters is incredibly creative.
The "drink-and-dial" scene is a great example of that.
Awesome underrated movie, absolutely recommended!