HBO on Amazon: What to Watch First?

By now you know the news that HBO will make a lot of its older content available to Amazon Prime subscribers starting May 21 as part of a lucrative deal. So where to begin?

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By now you know the news that HBO will make a lot of its older content available to Amazon Prime subscribers starting May 21 as part of a lucrative deal. The network's current top-tier content, like Girls and Game of Thrones, will remain off-limits to non-subscribers. But a rich vault of quality premium television is suddenly being opened up to a huge base of viewers, a prospect both exciting and daunting.

It goes without saying that the "holy trinity" of HBO original programming—The Sopranos, Deadwood. and The Wire—are pretty much worth watching from start to finish. Yes, one could debate which season is the best of each (obviously the answer is five, two, and four, but feel free to fight me on that). But I'm going to give a blanket recommendation to those three shows. However, here are some gem seasons of other HBO shows (a few original films) to start off with when the archive goes live.

Six Feet Under: Season Two

Six Feet Under was all that in its early seasons, grabbing hauls of Emmy nominations and briefly convincing HBO to expand its original programming into a Monday night slot. (A plan it quickly undid). But in retrospect, it's a very flawed show filled with a lot of broad generalizations about the human condition and increasingly over-the-top plot twists. In short, it's an Alan Ball show, the most quintessential. But it really was firing on all cylinders for its second season, which charts Nate's battle with a medical diagnosis, Claire's final year in high school, and Brenda's descent into sex addiction. And the finale "The Last Time" is something else. Cheesiness aside, Six Feet Under was more compelling than anything when it was working.

Rome: Season One

Now that Game of Thrones is in its fourth season, we definitely can't say there won't ever be a TV show as epic as Rome. But there's still something special about Rome, especially that first season. A ridiculous, massively-budgeted retelling of the rise and fall of Caesar, it had a bunch of solid actors doing the best work of their lives (James Purefoy, Ciaran Hinds, Polly Walker, Kevin McKidd, Ray Stevenson) and ludicrous amounts of sex and violence, celebrating the Roman empire as a debauchery hall-of-fame. The second season came apart at the seams quickly, but Season One tells a complete story and it does it very nicely.


Hey, has anyone at a dinner party ever told you, with the fervor of a missionary who has walked a thousand miles through the desert, to check out Enlightened? "But I don't have HBO!" you protested, a flimsy excuse for missing out on one of TV's greatest, most underseen gems of recent years. Your excuses grow flimsier by the second. It is time. There are only 18 episodes. If enough of us watch it, maybe it can come back. Don't ask any more questions.

Flight of the Conchords: Season One

Is this underrated? Probably not. Lots of people liked Flight of the Conchords when it aired, and the only reason it stopped airing was that the boys didn't want to do it anymore and had run out of original songs (which showed in Season Two). But even if you liked Conchords back in the day, it's time to revisit it and realize what a bulletproof comedy classic the first season is. Especially since we now have Broad City, another odd-couple show about life on the edge in New York City that's a worthy heir to the Conchords mantle.

Too Big to Fail

The "HBO Original Film About a Thing That Happened in the Recent Past" genre is largely overrated and exists only to collect Emmys for well-known stars. Things like Game Change, Recount, You Don't Know Jack, and others didn't even hold up for their first viewing. But Too Big To Fail, the chronicling of the 2008 financial downturn based on Aaron Ross Sorkin's bestseller, is actually still pretty good. Maybe it's just Curtis Hanson (a masterful director who has been slumming for over a decade now) recapturing his form. Maybe it's the typically star-studded cast, including James Woods, Paul Giamatti, William Hurt and Billy Crudup, who rarely get parts this meaty in film anymore. But this is the one HBO original film that's almost underrated.

When the Levees Broke

Yes, it's very long (more than four hours). Yes, much of it is very difficult to watch. But Spike Lee's detailed and sobering chronicling of Hurricane Katrina and its aftermath is some of his best work as a director and still stands as the definitive document of those events. It's well worth blocking off an evening for sometime.

What Isn't Mentioned?

Some really big shows like Sex and the City, Entourage, and Curb Your Enthusiasm aren't on this list, because HBO is keeping a tight rein on its content and won't give them away just yet. But what of its smaller, less-valued programs? Bored to Death, Carnivale, John from Cincinnati, and Luck are all waiting to be rediscovered as cult sensations by a whole new audience. When will that happen? 

This article is from the archive of our partner The Wire.