I am cursed (blessed) to keep running into Coolio. I never do anything more than wave or say hi, save for the initial meeting at the airport.
Saw him with a small entourage walking into the terminal as I was leaving. He had these weird braids in his hair and a DBZ shirt and One Punch Man hat on. I was dumbfounded and just blurted out "Coolio!?" And he looked up confused and saw me and I just said "Hey Coolio" and he just said "Sup?" and we both went on our separate ways.
To be fair, text-based humor is completely different from spoken humor. Shit, I've laughed at jokes that were inherently lame, but the way they were delivered was hilarious.