Ray Richmond is contributing to Deadline’s 2011 Emmy coverage. Here’s his scorecard assessing the Outstanding Lead Drama Series Actor race.

Jon Hamm, Mad Men
Why He Was Nominated: The question was never whether Hamm would be nominated. That’s a given. It’s his fourth in a row for his iconic Mad Men role of Don Draper but his first without three-time winner Bryan Cranston from Breaking Bad in the race due to that AMC show’s lack of eligible episodes. Many assume that Hamm has already won a couple of these things. The mystifying truth is that no performer from Mad Men has yet taken home an Emmy.
Why He Has To Win: Mad Men creator/showrunner/control freak Matthew Weiner is said to have specifically penned the episode “The Suitcase” as a performance piece for Hamm and co-star Elisabeth Moss (also nominated). It featured the two of them exclusively and powerfully. With Cranston out of the picture, there should be no keeping Hamm from his rightful cruise down victory lane. As a fellow actor and TV academy voters noted to me, “Everyone I talk to thinks the Emmy belongs to Jon this time. It’s well deserved and frankly overdue.”
Why He Can’t Possibly Win: Hamm hasn’t earned one of these things yet, and he’s been nominated for Emmys six times in all (also twice as a guest on 30 Rock). Plus, he’s up against two guys (Hugh Laurie and Michael C. Hall) who also have been nominated multiple times without winning. Either could well pull an upset.

Steve Buscemi, Boardwalk Empire
Why He Was Nominated: Because as the mob-tied politician Nucky Thompson on Boardwalk Empire, Buscemi was quite simply extraordinary. He’s already won Golden Globe and SAG awards for the portrayal. He’s also no stranger to the Emmys, logging his fourth nomination (honored for The Sopranos in 2001 for directing and supporting actor in 2004 as well as a 2008 guest nod for 30 Rock). Buscemi is still seeking his first win.
Why He Has To Win: Were Boardwalk to defy the experts and upend Mad Men en route to its fourth consecutive win for top drama series — a distinct possibility — Buscemi could easily ride those coattails. “He’s got the kind of feature pedigree that plays well to this crowd,” notes a series producer. Also bolstering his candidacy is the fact that James Gandolfini won for lead actor three times for The Sopranos in a role not significant different from that of Buscemi — and on the same network.
Why He Can’t Possibly Win: After Boardwalk premiered on HBO last fall to generally rave notices, Buscemi appeared to have the Emmy all but signed and sealed. That was before Hamm upped his game a couple of notches on Mad Men to become the frontrunner for the gold. But the truth is that Buscemi may not even be the second choice here in going up against the likes of Laurie and Hall. It’s a jam-packed category that could fall a couple of ways, and he’s no longer the favorite.

Hugh Laurie, House
Why He Was Nominated: Laurie always gets nominated and always deserves to win, too, even though he never has. He’s been tabbed six times (including five in a row) for his role as the mocking, unorthodox and brilliant Dr. Gregory House on the long-running Fox medical drama. He’s been beaten out by either James Spader (2005, 2007) or Cranston (2008-’09-’10). Neither of those guys is in the category this time. That’s the good news.
Why He Has To Win: It’s really about time. And occasionally, this is how it works at the Emmys. An actor comes up short numerous times and then, suddenly, wins one out of nowhere. Case in point: Kyra Sedgwick taking one in 2010 on her fifth try for TNT’s The Closer (and then wasn’t nominated at all this year). Laurie’s performance is consistently towering and indelible, and the riveting episode he’s submitted — “After Hours” — features him performing surgery on his own leg in a bathtub. Ouch.
Why He Can’t Possibly Win: Had Hamm not done what he did this past season on Mad Men, the award was probably Laurie’s to lose. “Hugh should have won in House’s first season,” believes a fellow actor and voting academy member. “With each passing year, it unfairly becomes increasingly less likely.” Such is life in Emmy Land. He’s also the only contender from a broadcast series, which at this point probably doesn’t work in Laurie’s favor.

Michael C. Hall, Dexter
Why He Was Nominated: It’s Hall’s fourth consecutive lead actor nod for his portrayal of warmhearted serial killer Dexter Morgan on the Showtime drama. He’s still looking to land his first win, but like House’s Laurie he’s a rock-solid part of the Emmy landscape.
Why He Has To Win: Nominated for the episode entitled “Teenage Landscape” that finds Dexter searching for killers while at the same time riddled with anxiety over his missing stepdaughter, Hall always merits serious consideration. One voting writer pointed out to me, “You know that you’re doing something right when you creep people out just by the way you look. That’s the vibe he embodies in this character.” Hall also snagged a SAG Award on his fourth nomination in 2010.
Why He Can’t Possibly Win: Last year looked like Hall’s time on the strength of his work on the season-capping episode involving his wife’s murder. This season’s submission doesn’t carry nearly the same explosive energy. That’s not to even mention his being up against Hamm and Buscemi. And if the academy is going to reward someone for their durability, it’s likely to be Laurie.

Kyle Chandler, Friday Night Lights
Why He Was Nominated: This is the second consecutive (and final) nomination for Chandler on the departed Friday Night Lights, which also grabbed nods for Outstanding Drama and writing as well as for Chandler’s co-star Connie Britton. It’s part of a late outpouring of appreciation for the beloved DirecTV high school football hour, one that could well be a statement about the longtime Emmy indifference shown the HBO drama The Wire.
Why He Has To Win: As heavy a long shot as he is, Chandler has both sentiment and the Lights cult of devotion going for him. The Big Bang Theory co-creator and showrunner Bill Prady, an unlikely hard-core fan of the series, marvels, “Kyle Chandler could do more with a clench of the jaw than a lot of people can do with a two-page monologue.” A lot of people both inside and outside the industry feel the same way.
Why He Can’t Possibly Win: The competition that Chandler faces here is huge, making for some mighty long odds. The fact that his show aired on satcaster DirecTV doesn’t much help, either. This is one instance where being really good simply isn’t enough. But the nomination alone is itself a victory, as even Chandler’s alter ego Coach Eric Taylor could agree.

Timothy Olyphant, Justified
Why He Was Nominated: While he’s making his maiden voyage at the Emmys, Olyphant is a proven commodity with a cadre of fans not just from his work as U.S. Marshal Raylan Givens in Justified but also from his luminous work on HBO’s Deadwood. That this nom proved a bit of a surprise is simply because the Sony Pictures TV series has been operating under the radar. That should change going forward given the sterling work of Olyphant and fellow Emmy nominees Walton Goggins and Margo Martindale.
Why He Has To Win: Travel with us back in time nine years to The Miracle of 2002, when a first-time nominee named Michael Chiklis engineered a huge upset in winning the lead actor Emmy for FX’s The Shield. He bested a similarly stalwart field that year that included Martin Sheen for The West Wing and Kiefer Sutherland for 24, among others. So it can be done. As a bonus, Olyphant’s work in the submitted Justified episode is singularly riveting.
Why He Can’t Possibly Win: This is no place for an Emmy first-timer to be hanging out. But of course, Olyphant has little choice in the matter. That it’s his initial invite to the Emmy party means he’ll be able to chalk up his likely loss to experience and return — like Marshal Givens — to do battle another day.