This is a pretty old dispute, but one worth keeping alive. Especially since Bungie has been dropping Halo content continuously since Halo 3, and Valve hasn't given us any clue as to when we can expect the much-anticipated conclusion to the Half-Life2 saga : Episode3!
Meh, I'll concede that Half-Life has the better story and characterization, and while interesting, Halo's just more fun for me. I like playing through the campaign with friends over and over, and I'm multiplayer for a little bit almost every night.
Granted the Orange Box does have Team Fortress 2, but that can hardly be counted as multiplayer for Half-Life. It's its own wonderful thing.