I think you need to distinguish between HBO Mini-Series and HBO Original Programming.
The Mini-Series are generally outstanding.
Band of Brothers is one of the finest things ever put on TV.
From Earth To The Moon is simply epic and if you have even a passing interest in history and science it’s incomparable.
Generation Kill was very good. It’s not on the level of Band of Brothers, but it’s a very interesting modern look at war and a interesting group of characters.
John Adams was a terrific period piece but thought parts of it got a little too PBS/Nova-like towards the end. The early scenes where they debated declaring independence were hugely powerful though.
There are others and off the top of my head I can’t think of any that were disappointing.
The Original Programming was more hit-or-miss.
The Half-Hour Comedy Series tend to be short lived failures for the most part, even if some are critically acclaimed and cult favorites.
Entourage is a favorite of mine. I see that it’s not for everyone, but as a single guy it’s in my wheelhouse.
Lucky Louie was a short lived, vulgar sit-com filmed on a live stage that was very unique. I found it hilarious but it didn’t last.
Flight of the Conchords is very popular if you like quasi-British style humor, filled with absurdity and sarcasm.
Curb You Enthusiasm has been hilarious but it’s a little too thick with “awkward comedy” for my liking. Though, I’m in the minority on that I think since it was so successful.
The Hour Dramas have been more successful, and are generally worth the time even if some are a tad over rated.
The Sopranos is a classic.
The Wire is one I never got into, but it’s universally said to be great.
In Treatment was painful to watch, and fucking dull.
John From Cincinnati was a clusterfuck. Spare yourself the grief.
True Blood is fun, great if you are a vampire fan. The characters are pretty badly developed and unlikable and I found the story deteriorating as the season ended but I watched anyways. It was very popular so it’s safe to assume that it’ll be around for a while.
Rome was one of their best. The fact that it was intentionally short-lived makes the story feel happily complete and satisfying.
Tell Me You Love Me had moments, but it was a little too melodramatic to last. It was a bit self-serious.
Six Feet Under is a show I’ve always hated, but people around here love the thing. Decide for yourself I suppose, it’s worth trying since many people love it more than words.
Deadwood. See Six Feet Under.
Big Love. See Deadwood.
Then there’s the Reality Shows.
Cathouse is kind of it’s own thing. It’s a quasi-Reality show set in a real brothel. It can be entertaining and it’s got lots of sex and nudity, but it’s got no story arc and is something of a freak show at times.
Taxicab Confessions was pretty revolutionary and many of the episodes were simultaneously hilarious, sad and erotic. Very worth watching.
Autopsy with Dr. Baden is better than any CSI/Law And Order show ever made. Occasionally it’s a little gruesome with the real-live footage, but it’s educations and compelling.
Real Sex is stupid, perverted fun. Half the people in there should never be seen naked but the depths of human sexuality is entertaining. It’s pretty damned dated though.
I know I felt out a bunch but I have to run. More often than not an HBO show is worth trying. One thing I feel safe saying is that the shows are consistent. If you don’t like the first 4 episodes it’s safe to assume that you won’t like the rest and vice versa. Some of the long running ones have peaks and valleys, but there just aren’t that many that last long enough to jump the shark.
FTR, Arrested Development was never an HBO show.