I've gotta say, the people coming up with bounties are incredibly creative. I really liked these ones:
Walk Of Shame - 1st player to die from your team must walk from one side of the river to the other without leaving the river while their team spams "SHAME SHAME SHAME". If the player dies on the way, they either give up, receiving no moonbucks, or try again.
Sacrifice - Deny an item, all chat what it was. If the enemy denies a more expensive item, they get the bounty instead. You may one-up their deny and so on and so forth. When the first rax of the game falls, the bounty ends. Doesn't double if you win.
Treasure Hunt - Hide a bottle in the enemy jungle and announce treasure hunt in the all chat if after 5 mins the enemy doesn't find the bottle you win moonbucks.
Edit: Finally started to watch the OG/MoF game 1 and the trivia was fucking hilarious. Also liked whoever on OG (n0tail?) that congratulated Synd on the correct answer, then said "now try playing some dota."