Crowning Music of... Funny?: The musical switchups during Robin and Little John's staff fight. It gets faster and sillier the shorter their staffs get, then finally turns into a chirpy, cartoonish ditty when they're reduced to smacking each other's knuckles with sticks.
This was Dave Chappelle's first film. Who would have guessed he would later make a successful and over-referenced gag out of a guy named Lil Jon?
Will Scarlett O'Hara is played by Matthew Porreta, who played Robin Hood later on in a TV series. note Which was riding on the popularity of Kevin Sorbo's Hercules series at the time, rather than any Robin Hood property. There was also a Sinbad series then. They replaced him in the role long before it was discontinued.
A minor one, but the Italian assassin who Don Giovanni dispatches to kill Robin? His name is "Dirty Ezio."
Cary Elwes makes fun of Kevin Costner's terrible British accent in this film. Later, Elwes famously attempted an American accent in Saw and failed spectacularly.
Ho Yay: Prince John and the Sheriff of Rottingham, in spades.