Ray Richmond is contributing to Deadline’s 2010 Emmy coverage. Here’s his scorecard assessing the Outstanding Lead Drama Series Actor race:

BRYAN CRANSTON, BREAKING BAD

Why He Got Nominated: He’s won two years running, and the TV Academy isn’t in the habit of failing to nominate guys who won the year before (except in rare instances). Plus, if anything, Cranston just enjoyed his best season onscreen.

Why He Has To Win: The episode Cranston submitted to voters, “Full Measure”, was the season-ending cliffhanger that shows his character  continuing a mindbending personality transformation. Voters like it that kind of risk, particularly when the judges are teams of acting contemporaries. Believes one of those voters: “This man isn’t merely acting. He’s creating art.” Also his performance is fresh in voters minds, since the show’s season finished in June.

Why He Can’t Possibly Win: The AMC show’s ratings are still comparatively miniscule, which could hurt Cranston’s bid to three-peat. There’s also tough competition from Jon Hamm and Michael C. Hall for their own breakthrough seasons.

JON HAMM, MAD MEN

Why He Got Nominated: No one in the Industry can overlook AMC’s Mad Men or Jon Hamm come Emmy-time. Plus, the actor has shown his range with guest appearances on 30 Rock and SNL. Now more than ever, the TV Academy knows he’s the real deal.

Why He Has To Win: After two earlier years as the heavy favorite, he’s not this year. That means a win would be unexpected, which is the TV Academy’s way of showing he was overdue. Plus, Hamm’s submitted episode “The Gypsy and the Hobo” is a whopper of an acting showcase. He also happens to be exceedingly well-liked on set and in the acting community because he hasn’t let the fame and praise go to his head.

Why He Can’t Possibly Win: It’s possible that the TV community’s fixation on the show’s behind-the-scenes dramas starring Matthew Weiner doesn’t extend to the actors. Or why else would none of the thesps have won in Mad Men‘s first 2 years of eligibility despite multiple nominations? As for Hamm, surely the Academy isn’t naive enough to think that just because he makes playing Don Draper look easy, it is.

MICHAEL C. HALL, DEXTER

Why He Got Nominated: This is Hall’s 3rd consecutive nomination for Showtime’s Dexter, and his 4th overall (earning one for Six Feet Under). He’s recognized for consistently taking his game to a new level in this show.

Why He Has To Win: He’s submitted the edgy but wrenching season-ender “The Getaway” for consideration, which may be his best work to date. But there’s also buzz that it’s time to reward Hall. It’s ridiculous that Hall has never has won, a fact the TV Academy may want to rectify since he snagged the SAG Award on his fourth nomination. This is hardly a sure thing, of course: the voters revel in upsets. But if ever Hall were going to win, this would be the year.

Why He Can’t Possibly Win: There’s an “out of sight, out of mind” aspect to Emmys, and Dexter ended its season way back in December. Too, as one producer puts it, “There are some voters who are never going to vote for a guy who plays a serial killer.”

HUGH LAURIE, HOUSE

Why He Got Nominated: Laurie always gets nominated. That he never wins doesn’t discount the fact he deserves to be noticed at Emmy-time. It’s his 6th nomination for Fox/Universal Media Studio’s House – 5 for acting, and one for producing. Voters appreciate his consistently fine performance in a challenging role.

Why He Has To Win: It’s giving it to Laurie for his body of work at this point. Laurie did manage to earn SAG Awards in 2007 and 2009. But that doesn’t necessarily score points with Emmy judges. This might: his submitted episode is the 2-hour Broken that puts him in a psychiatric hospital going through Vicodin detox. If voters are inspired, it could tip the scales in his direction.

Why He Can’t Possibly Win: History. Rarely does an actor who is a previous 4-time Emmy loser win on the 5th attempt.

MATTHEW FOX, LOST

Why He Got Nominated: He was probably due after predictions he would be nominated after Lost‘s previous seasons. The fact it was the final season following an ABC publicity blitz no doubt made the difference.

Why He Has To Win: The Lost finale grew into a national phenomenon, and that’s going to be key to his Emmy chances given that he submitted that episode (“The End”) to voters who were able to watch it live, which cemented perceptions. Also, it received healthy ratings. He now has a body of work if Party Of 5 is included. Also bolstering his chances is that he’s an affable guy, and his fellow acting types after all are judging him.

Why He Can’t Possibly Win: He’s not yet at the same level as Cranston, Hamm, or Hall. And the buzz accompanying his work this past season isn’t exactly deafening. It may take a 3rd series to win him the Emmy.

KYLE CHANDLER, FRIDAY NIGHT LIGHTS

Why He Got Nominated: This is as pure a nomination as there is at the Emmys this year, after Chandler emerged from the pack in a show everyone has long raved about but now mostly ignored on DirecTV. Chandler’s acting, not reputation or quid pro quo, made this happen.

Why He Has To Win: Chandler gave an indelible performance in his submitted episode “East of Dillon”. The TV Academy sometimes decides seemingly en masse to make an upset happen for all the right reasons, and this would be that. “If this guy’s show didn’t air on DirecTV,” believes one producer, “he’d be a shoo-in.”

Why He Can’t Possibly Win: His show airs on DirecTV.