Gamefly might not like me saying this, but don't even bother renting The Orange Box. This is a definite buy!
Portal alone is worth the majority of the cost. Portal is one of the most innovative and rewarding games I have ever played!
Team Fortress 2 (as expected) is a blast. It's cartoon look actually helps the game out a lot. Some games (for example Gears of War) really give me some trouble when it comes to telling the difference between the characters in multiplayer. Because of the cartoon-like characters in TF2, it is easy as cake to tell who is who in a fast paced game (which is vital because it is, after all, TEAM Fortress).
As for Half-Life, you get Half-Life 2, Episode 1 and Episode 2, which are 3 different games, and if you're a fan of the Half-Life franchise, these are sure to keep your attention.
I wont keep this short and simple: this game contains 5 games in one, and it doesn't skimp on you either. There is the original Half Life 2 which took me about 10 hours to beat, Half Life 2 episode 1 which took me about 4 hours to beat, Half Life 2 episode 2 which was amazing fun and took me about 10 hours to beat ( i enjoyed every minute of it except for the mines in the beginning).
After you finish the half life 2 saga you can test your mind against the puzzles of Portal, which pits you in a series of physics based challenges, which i found rather addicting even though I personally have very little interest in puzzle games. Once your done with all this single player content there is yet even more to see and do with the multiplayer component Team Fortress 2. Don't let the cartoonish character model's fool you; this game is intense. With the various character classes how you play is up to you. You can be strategic as a spy or engineer, or you can jump straight into the fray as a soldier or pyro.
Any way you look at it this game will keep you occupied far longer than the countless other games that have been released lately, so if your a video game player who gets frusterated with plucking out the cash for a game that only gives you 10 hours of entertainment, than you may be in for a treat with this one.