Webcomics 20 Comic Strips That Are Hilariously Depressing  

Stephen Reyes
72.4k votes 13.2k voters 655k 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 3,720 VOTES

Real Treasure

Real Treasure is listed (or ranked) 1 on the list 20 Comic Strips That Are Hilariously Depressing
Photo:  It's the Tie/Mr. Lovenstein
3,083 637
Is this funny, but sad?
2 4,403 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
3,633 770
Is this funny, but sad?
3 4,161 VOTES

Spring

Spring is listed (or ranked) 3 on the list 20 Comic Strips That Are Hilariously Depressing
Photo:  ardenthusiast
3,437 724
Is this funny, but sad?
4 4,661 VOTES

Living Worth

Living Worth is listed (or ranked) 4 on the list 20 Comic Strips That Are Hilariously Depressing
Photo:  J.L. Westover
3,840 821
Is this funny, but sad?