2008 Emmy Preview: Best Supporting Actor Comedy

The Emmy for Best Supporting Actor Comedy honors TV comedy’s greatest second bananas. Famed comedy sidekicks like David Hyde Pierce, Michael Richards, Brad Garrett and Sean Hayes have been most recently honored for matching and often upstaging their leading comedic men. Lately, Jeremy Piven has been dominating this Emmy category much like those previous scene stealers have. This year at Emmy time, Piven is facing the exact same four nominees he defeated last year. But this time around, one of them could dethrone Ari Gold.


Jon Cryer as Alan Harper, Two and a Half Men: for episode “Meander to your Dander”
Kevin Dillon as Johnny “Drama” Chase, Entourage: for episode “The Dream Team”
Neil Patrick Harris as Barney Stinson, How I Met Your Mother: for episode “The Goat”
Jeremy Piven as Ari Gold, Entourage: for episode “The Day F**kers”
Rainn Wilson as Dwight Schrute, The Office: for episode “Money”

Piven goes for a three-peat in this Emmy category, which hasn’t been accomplished since John Larroquette did it for Night Court in the 80’s. But Piven has been a dominant winner for the last two years as Entourage’s signature character, super agent Ari Gold. Piven’s bravado and spoofing of Hollywood agents that the voters would easily recognize has paid off big for him, so he has to be a favorite to do it again. For his submission tape, Piven gets to go off in typical Ari fashion once again as he squares off with the headmaster of his son’s private school.

Despite Piven not losing any buzz, a few of his Emmy competitors may have found room to gain on him. The Emmy nominee with the biggest career boosts around him is Neil Patrick Harris. Harris is nominated for the second straight year as the womanizing Barney on How I Met Your Mother. Even though the show continues to be on the rating bubble, the raves that Harris gets for it, plus his growing celebrity, have helped keep the show alive. Harris’s coming out last year, his infamous Harold and Kumar cameos, his Internet musical series and his Old Spice commercials have given Harris a greater fame than he ever had as Doogie Howser. All Harris’s run of success is missing is an Emmy, and with a submission tape where Barney sleeps with his best friend’s ex and then loses his “bro”‘s friendship, it might have the best shot to end Piven’s Emmy run.

Another rising star that could make up some ground is The Office’s assistant regional manager, Rainn Wilson. Also nominated two years in a row, Wilson plays the category’s weirdest character, Dwight Schrute. In Wilson’s submission tape, Dwight runs the world’s creepiest bed-and-breakfast from his family farm, when not mourning the end of his secret office affair. Like Steve Carell, Wilson occasionally faces uneasiness for playing a creepy, often unlikable character that hasn’t translated well with Emmy voters yet. Piven and Harris, for all their own over-the-top antics, are probably easier for most voters to accept. But Wilson’s tape is a two part episode, so more screen time could help him if voters aren’t put off by Dwight.

Kevin Dillon also returns to the Emmys as Entourage’s other head scene stealer, Johnny Drama. Dillon is usually regarded as the only Entourage character that can match Piven, also fitting a traditional Hollywood role as the less successful brother of a movie star- which the real life Dillon technically is himself. In Dillon’s submission tape, he goes to great lengths to get a medical marijuana prescription- just to get a cap that’ll make him look younger. But although Dillon plays his own important part in powering Entourage, as long as he’s on the same show as Piven, it will be harder for Dillon to upstage him on the show and on Emmy night.

The last Emmy nominee is another CBS supporting actor, Jon Cryer. With his third straight nomination for Two and a Half Men, Cryer is the challenger that’s gone the longest with no Emmy success. Cryer is on CBS’ biggest comedy show, which is usually a favorite to get Emmy nominations despite objections from some critics. However, although Cryer, his co-stars and the show usually get to Emmy night, they have yet to win a major Emmy. Despite a tape where Cryer’s Alan gets typical awful advice from Charlie Sheen about how to break up with a girl, Cryer still has an uphill battle to pull off an upset.

This Emmy category has had some of the suspense taken out of it lately with Piven’s wins and the same few people getting nominated. But as Piven’s reign enters it’s third year, this may be the best chance for the likes of Harris or Wilson to take over. Yet even if it is, this is one Emmy category where the same few people tend to win every year, having earned enough goodwill to keep repeating. If the Emmy voters want to change things around this year, they’ll probably go with Harris. But if Piven still has the juice with enough voters, he will hug out a third Emmy.

Projected winner: Jeremy Piven