I just think the juxtaposition of the solemn look on his face and the cap is hilarious, like he's thinking 'its tough at the top'. If you have $145 to spare you can get one of those caps for yourself.
Also, I like tigers.
a large bit of graffiti in Sheffield city centre, visible from Netherthorpe Road tram stop
your man(?) VOMIT gets around a lot - besides Sheffield, there have been multiple VOMIT sightings in Derby and Nottingham as well (this one made me laugh)
the best one I've seen is a great big tag on the shutter of a derelict warehouse, where he(?) missed out the I, so it says VOMT; a nice bit visual schadenfreude