so... that's your answer. that's the only way to make it stay on top. winamp (i'm assuming your using version 2, but it applies to 3 also) doesn't have a definite size, you can change the playlist height and width, and it's impossible for windows to maximize and change the border to wrap wround the object. even if you did stretch winamp the entire length of your screen, window's still won't register it. sorry.
[Okay, how do I know you're wrong if you're just guessing?] [NTO GODO!1]
well, actually, there sort of is get bandit - http://www.holesoft.com/bandit/index.htm - and capture it into your taskbar. I haven't played with bandit at all, as I actually like my winamp in windowshade mode, and my taskbar is already a @#$%ing mess without whacking winamp in it :) there's no way built into winamp though. wish they would, that'd be effing magnificent.
and, dogbert, that logic is a little flawed. you can resize AIM till your hearts content, but it still has it built in. Not much is impossible in windows, it just restricted by how lateral the coder wants to start thinking.
aha, found the other one I was looking for. use HawkEye ShellInit to restrict the maximized size of windows, so they don't cover winamp. get it at http://www.hawkeyetech.com/products/freeware.htm
and the third one. damn, my googling is a bit rusty today. Seelsoft (one of the guys from skinz.org msgboard if i remember correctly) WorkTop does the same as shellinit. once again, haven't played with this app, i remember it being a little buggy. anywho, get it at http://www.virtualplastic.net/html/top_10.html (5th link down)
actually you could build in winamp onto the desktop with an html script on active desktop which would place buttons on the dtop each corresponding to a winamp control (play, paus, stop, ff, rew) and then add another html script (or use samurize) to have it show on the dtop which song your playing. then load your songs via explorer by double clickin each song. so it can be done.
:: Azmyth - Customize.org Admin :: :: Arguing on the internet is like competing in the special olympics. Even if you win, your still a retard ::
Hawkeye ShellInit. A small, scriptable application that "creates any number of margins on the screen that maximized windows wont cover (much like the taskbar). In these margins, you can put applications that you always want visible, for instance Winamp, SysMeter, console, chat window, or whatever." Can run automatically at startup.