Webcomics 20 Comic Strips That Are Hilariously Depressing  

Stephen Reyes
72.6k votes 13.2k voters 655.8k 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 4,681 VOTES

Living Worth

Living Worth is listed (or ranked) 1 on the list 20 Comic Strips That Are Hilariously Depressing
Photo:  J.L. Westover
3,859 822
Is this funny, but sad?
2 3,738 VOTES

Real Treasure

Real Treasure is listed (or ranked) 2 on the list 20 Comic Strips That Are Hilariously Depressing
Photo:  It's the Tie/Mr. Lovenstein
3,098 640
Is this funny, but sad?
3 4,176 VOTES

Spring

Spring is listed (or ranked) 3 on the list 20 Comic Strips That Are Hilariously Depressing
Photo:  ardenthusiast
3,450 726
Is this funny, but sad?
4 4,421 VOTES

Glad I Found You

Glad I Found You is listed (or ranked) 4 on the list 20 Comic Strips That Are Hilariously Depressing
Photo:  Ryan Hudson
3,647 774
Is this funny, but sad?