You can only get the upgrade for Sly during Two-Player Mode. You can't get it in the actual story mode. However, you can play as Carmelita, and she can charge her mega jump by holding down the circle button.
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there is 4 games of the sly cooper franchise.3 of them are ps2,and sly cooper 4 is going to be for the ps3,coming out in 2012,this awnswer was made in november 2011.but after sly cooper 4 there MAYBE will be more.
Carmelita Fox is around the same age as the members of the Cooper gang, and a specific age is never stated but as of Sly 3 they are in about their early twenties.
No, he just fakes it. If you watch the credits on Sly 3, Bently is looking at Sly and Carmalita through his Binocucom and Sly turns to him and winks. Bentley responds by saying "That sneaky devil!"
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You can not play the actual game with a friend but there are mini-games that you can play with one other friend.