Webcomics 20 Comic Strips That Are Hilariously Depressing  

Stephen Reyes
67.9k votes 12.4k voters 638.9k views 20 items

Is there anything more bittersweet than comics that are both funny and sad? They hit you right in that sweet spot that makes you smile and feel like your gut has been punched at the same time. Depressing comics have been a mainstay on the Internet for a long time, and over the years aspiring illustrators have mastered the art form.

Vote up these unbelievably funny and depressing comic strips, particularly the ones that made you laugh and feel terrible at the same time.

1 3,608 VOTES

College

College is listed (or ranked) 1 on the list 20 Comic Strips That Are Hilariously Depressing
Photo:  Yesterdays Popcorn
2,981 627
Is this funny, but sad?
2 4,083 VOTES

Glad I Found You

Glad I Found You is listed (or ranked) 2 on the list 20 Comic Strips That Are Hilariously Depressing
Photo:  Ryan Hudson
3,361 722
Is this funny, but sad?
3 3,877 VOTES

Spring

Spring is listed (or ranked) 3 on the list 20 Comic Strips That Are Hilariously Depressing
Photo:  ardenthusiast
3,195 682
Is this funny, but sad?
4 3,176 VOTES

Promotion

Promotion is listed (or ranked) 4 on the list 20 Comic Strips That Are Hilariously Depressing
Photo:  Zach Weinersmith
2,632 544
Is this funny, but sad?