Wouldn't really consider it obscure, but I do not hear people saying much about it. After Life with Ricky Gervais...for anybody that has experienced or still going through deep grief, it is as relatable and therapeutic as it gets.
Joe Pera Talks with You on Max. It originally aired on Adult Swim and is just a mild-mannered choir teacher in Michigan's Upper Peninsula talking about stuff. It's not really plot driven but there are story arcs. It's difficult to describe, but it's really funny. Highly recommend the episode where, instead of reading the church announcements, he talks about having just recently heard "Baba O'Reilly" for the first time.
Arlington Road is a fantastic movie that never really got much attention. Bonus is was filmed in the Houston area.
I cannot stand Woody Allen the actor or person, but Midnight in Paris was a great movie Sidewalks of New York (no woody) Colors Troll Hunter Used Cars
Pretty much all Alex Cox films. The one that might be most obscure and would be close to my favorite is Straight to Hell.
I haven't seen all of these but the top 3 are absolutely amazing. Based on those, I'll check out the others.
Saragossa Manuscript The Wailing Tampopo Just a few that I have watched again recently that I absolutely adore.