Webcomics 20 Comic Strips That Are Hilariously Depressing  

Stephen Reyes
71k votes 12.9k voters 648.9k 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 3,621 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
3,001 620
Is this funny, but sad?
2 4,318 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
3,562 756
Is this funny, but sad?
3 4,065 VOTES

Spring

Spring is listed (or ranked) 3 on the list 20 Comic Strips That Are Hilariously Depressing
Photo:  ardenthusiast
3,358 707
Is this funny, but sad?
4 4,139 VOTES

The Greatest Gift

The Greatest Gift is listed (or ranked) 4 on the list 20 Comic Strips That Are Hilariously Depressing
Photo:  Alex Culang and Raynato Castro
3,417 722
Is this funny, but sad?