It is much like the word bittersweet
in that it is something that is both rough
(bad) and nice
(good) at the same time. it originated based on events in college such as hooking up with a very ugly
girl or taking too big of a hit
off of the bong
and then coughing uncontrollably.
"Dude, i hooked up with Ariel
"Last night i took twenty-two shots
last night and woke up in my vomit
on the side walk, but from what i remember it was the best night of my life."
Or even: A suicide kill on Super Smash Brothers