If you want to kill more time and money then you actually have (and this applies of regardless of how much time or money you ever have) pick up Warhammer 40k.
For board games, my friends and I enjoyed playing Arkham Horror (as other people have suggested), but lately we've been enjoying a tabletop called Mouse Guard RPG. It's based on a comic book, but you don't need to read it in order to enjoy it. It's very story and character oriented, and you only really need the rule book and character sheets to play. If you're looking for an experience of collective story-telling and like the idea of a fantasy RPG with mice and other animals (or maybe if you read & liked Redwall), I'd highly recommend it. The way it is designed, you can have these huge conflicts/battles where the struggle can be anything from an actual fight, to trying to survive a storm, or an interrogation...whatever the GM can imagine...in our last session the big conflict was a dam we built versus a river in order to save a town from flooding.
Miskatonic School for Girls is a really fun deck-building game for up to four players. Essentially, each player is a house of students, and you have to spend each turn recruiting friends and fighting off teachers/mind-rending horrors from the deep. Each player starts with twenty sanity, and the last one to stay sane wins.
Sentinels of the Multiverse has completely taken over our gaming night. It's a superhero character based, co-op card game. Each character, environment and villain is represented by a deck of cards. Each player chooses a superhero and plays from their deck. Together you try to take down the villain - who is actively trying to kill you - in an environment - which vary from more-dangerous-than-the-villain to actively-helping-you-take-him-down to possibly-ending-the-game-on-its-own-by-wiping-everyone-out. There are thousands of different possible combinations of heroes/villains/environments.
The mechanics in this game are genius. Every time we play something different happens: from near-instant victory/defeat to three hour long slug fests where it's never quite clear who's going to win. Sometimes circumstances conspire into hour long slug fests where the victor is quite clear the entire time that kind of suck, but it's still kind of fun playing a table top game that's not afraid to occasionally slowly wipe the floor with you. That and you can never count out some crazy-ass card popping up that saves you from your previously inevitable death, or robs you of your surefire victory...
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