Finding that out-of-the-box holiday gift for the guy in your life is always a challenge. You don't want the gift to be so silly that he'd never use it, but you also want to make sure it gets a reaction out of him. Let's face it: that three-pack of t-shirts you give him each year just isn't cutting it. So whether he's a cocktail connoisseur looking for a new challenge or he spends his evenings rewatching old episodes of The Office, we have 19 holiday gifts that are sure to put a smile on his face. Time to start shopping!