Webcomics 20 Comic Strips That Are Hilariously Depressing  

Stephen Reyes
72.9k votes 13.3k voters 656.8k 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 4,702 VOTES

Living Worth

Living Worth is listed (or ranked) 1 on the list 20 Comic Strips That Are Hilariously Depressing
Photo:  J.L. Westover
3,877 825
Is this funny, but sad?
2 4,444 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
3,668 776
Is this funny, but sad?
3 3,759 VOTES

Real Treasure

Real Treasure is listed (or ranked) 3 on the list 20 Comic Strips That Are Hilariously Depressing
Photo:  It's the Tie/Mr. Lovenstein
3,115 644
Is this funny, but sad?
4 4,192 VOTES

Spring

Spring is listed (or ranked) 4 on the list 20 Comic Strips That Are Hilariously Depressing
Photo:  ardenthusiast
3,463 729
Is this funny, but sad?