One of the more interesting gambles when you go to Las Vegas occurs not in the casino but at the hotel check-in desk. Not everyone knows about this and not everyone tries it but those who try it think it's a better wager than doubling-down on 11 when the dealer's showing a six.
When checking in, you have a twenty dollar bill at the ready. You let the desk clerk see it and you say, with a casual manner and an air of nonchalance, "Uh, any complimentary upgrades available?" Translation: "If I give you this twenty, will you give me a better room for the same price?"
There are, of course, variations. Some flash more than twenty. Some try to get by with less. Many think the way it works — or works best — is to fork over the gratuity and then ask. If you do this and the answer is "no," the clerk may or may not feel it's sporting to return the cash, which is where the real gamble occurs. If you don't fork it over regardless, then the gamble is that you'll be embarrassed and perhaps feel like a hick tourist with no juice. In Vegas, it's okay to lose your money but you don't want to lose the illusion that you're important.
Does it get results? Sometimes. Conventional wisdom is that it's more likely to work with male clerks than female — I have no idea why — and that your best chance is when you check in late in the day because that's when they have a good idea as to how many rooms may go vacant that night and what class of rooms. Also, of course, if you're there on a crowded weekend or during a big convention, you may feel privileged just to get the room you booked, never mind any improvement.
My own experiences suggest that it will often yield better accommodations if (a) the town is not jammed and (b) the clerk seems friendly and in a chatty mood. It also helps to bring it up before he goes through the whole procedure of assigning you that crummy room next to the glopeta-glopeta ice machine that you'd rather not have if you can help it. And it doesn't hurt to act like you're used to getting upgrades this way and that you're kind of a regular visitor to the hotel…you know, the kind of guy who might be about to go drop a couple thou at a craps table.
If you want to know more about this form of institutionalized bribery, there's a website that's wholly devoted to how and where it's succeeded and how often. I don't know how much stock to put in the reports there but I know that like everything else in that town, the $20 Bill Trick pays off…sometimes. What I've never been able to find out — and now that I'm admitting it here, I'm sure someone will write and tell me — is how the hotels feel about it and if the employee keeps all or part of the money. Management knows this goes on and I can't imagine why they'd let the guy behind the front desk make all that extra cash.