The Tour Stop: Toronto (April 14 and 15 at Massey Hall)
The Rapper Charlie Should Invite: Drake
How He'll Help Charlie Keep Winning: Drizzy is the biggest celebrity in T-Dot right now. And since Charlie's got two dates booked there, it would be smart to get him to show up to at least one of them. Plus, we're pretty sure Charlie wouldn't mind meeting Drake's labelmate Nicki Minaj if he can swing it. You could probably make room for a third "goddess," couldn't you, Chuck?