I discovered Sports Night by accident on one of the digital channels whilst waiting for another show to come on. I'd recently become hooked on "The West Wing" and suddenly realised the reason I liked SN so much was that it had the same amazing quality of writing - and, on closer inspection, several of the same actors.
Set behind the scenes of a late night cable sports show, SN is a study of workplace relationships. It's a comedy (pity about the dreadful laugh track on the first few episodes), but like any of Sorkin's stuff, it can make you laugh, cry and learn something new within any episode.
The cast and crew are amazing and if you watch carefully, you'll see Mr Sorkin reprise his trademark role of "Man in Bar" from both "A Few Good Men" and "The American President".
It's a shame it's never been released in a R2 format, but if you've got a multi region DVD player, get it. It's definitely worth it. The Anniversary edition has additional commentaries by the cast and crew, but those are just the icing on the cake.