The Greatest HBO Character of All Time: Day One

Let’s get this started. I laid out the bracket, the rules and some initial thoughts yesterday. Today we’re going to get things cracking with round 1 of the Soprano Bracket.

1. Tony Soprano (The Sopranos) vs. 8. Sookie Stackhouse (True Blood)

Not really much of a contest here unfortunately. Even if she is an often hot & occasionally very hot fairy, Sookie really doesn’t stand a chance when matched up again Soprano. We don’t even need to get into arguments about cultural significance or importance on their respected shows. You could even make the case that Sookie isn’t even the best character on her show and that if anything, she could be replaced in this tournament by Lafayette. Tony wins this easily. But before we move on, we’ll at least give Sookie some dap for this scene.


Winner: Tony Soprano

4. Bubbles (The Wire) vs. 5. Flight of the Conchords (Flight of the Conchords)

Okay, this is more like it. Our first interesting match up. Bubbles was the Shakespearean fool of The Wire and his heart-wrenching journey from hopeless drug addict to hopeful recovering addict was one of the few stories in The Wire you could walk away from feeling good about. Meanwhile, the Conchords, Bret and Jermaine, had a brilliantly funny and amusing sketch comedy show that while only lasting two seasons left a handful of great songs stuck in your head. You know, like this one:


But is that enough? I mean, Bubbles was funny too. Him calling McNulty “McNutty” never really got old and as previously mentioned, he was really one of only a few characters to end The Wire on a good note. Homeboy kicked a crippling drug addiction! I’m sorry Conchords, but you barely kicked an addition to hair gel. Bubbles wins this one, but just know, I don’t feel totally great about it.

Winner: Bubbles

3. Nucky Thompson (Boardwalk Empire) vs. 6. Margaret Thompson (Boardwalk Empire)

Ouch. This is awkward. I mean, they’re married. Kind of.

Let’s take personal issues out of this. It’s too messy. Kind of like their relationship. No! Personal politics are removed!

We’ll look at Margaret first. She overcame a drunk and abusive husband and became an advocate for woman’s reproductive rights in Atlantic City. That’s an admirable journey. But wait a minute- she overcame the drunk and abusive husband because Nucky had poor Mr. Schroeder killed. And yes, Margaret ended up doing some great things at the hospital but that’s due largely in part to the generous donation she gave the hospital- a donation that was funded by Nucky’s money. Man, this is messy too.

Nucky is the star of the show. The show revolves around him. Even when it looked like the show was drifting away from him in season 2, it still ended up coming back in his direction. Season 3 ended with him re-establishing himself and reaffirming his grip on both the town of Atlantic City and the show Boardwalk Empire. Margaret ended last season essentially on the lam, trying to turn her back on the questionable choices she had made (and she made quite a few.) She put all her eggs (literally) in Owen’s basket, but when he ended up dead, it shot her plans of a marvelous new life in St. Louis in the foot.

You can’t discredit the role Margaret plays on the show and the voice she gives to the rising tide of feminism that was happening in the early 1920’s. It’s an important role and Kelly Thompson kills it. She goes toe to toe with Steve Buscemi’s Nucky and was never better than during season 2, when she took the reins of their relationship when Nucky was at a loss.

But still…

I’ve never been cool with the disconnect between how she acts and how her acts are paid for. I got no loves for hypocrites. At least Nucky knows who he is.

Winner: Nucky

2. Al Swearengen (Deadwood) vs. 7. Kenny Powers (Eastbound and Down)

Two strong as bull, tough-talking alpha males. One (Swearengen) was a pimp and saloon owner in the old west. The other (Powers) is a washed up ball player on a quest for redemption. I use the present tense for Powers because Eastbound and Down was recently renewed for a fourth season. The legend of Kenny Powers continues.

How to pit these two against each other is a tough one. How can we measure up two powerful dudes known for their rhetoric and bombastic style?

Let’s go to the tape.

First, some pick me up advice from Swearengen.


Now, some words of wisdom from Powers.


Hmmm…that didn’t really help. Granted I’m inspired now, but still undecided.

What does Frankie have to say?

“He’s (Powers) funny but he is super hatable. Half the episodes in a season I keep thinking, ‘what an absolute asshole’ and it kind of ruins him for me. But you gotta love him simply based on his k-Swiss commercial.”

Unfortunately Frankie has never watched Deadwood, which does count for something. He’s from California and I’m from Maine. So that essentially means America is weighing in on this decision, which should also count for something.

Final verdict?

Kenny Powers rocked corn rows for half a season while living in Mexico and betting on cock-fighting. Al Swearengen only lasted three seasons and never rocked corn rows.

Winner: Kenny Powers

Next up?

The first round of the McNulty Bracket.

Pictures- HBO

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