A top-of-the-line custom 1911...if money was no object, my choice would be a Bill Wilson Signature Edition:
http://www.wilsoncombat.com/p_limited.asp
My personal gun is a Wilson Master Grade, built by Bill Himself when he and I were writing THE COMBAT .45 AUTO back in the early 1980s.
Revolverwise, an S&W Triple-Lock .44 Special from about 1910. IMHO, the Triple-Lock is the finest revolver ever made on earth in the most perfect caliber. If I couldn't find a perfect one, I might accept a beater, have Hamilton Bowen at Bowen Classic Arms rebuild it and Doug Turnbull at Turnbull Restorations refinish it. Here's the Wikipedia entry:
http://en.wikipedia.org/wiki/Triple_lock
My personal gun is a custom Hamilton Bowen M28 S&W, vintage 1958, that he converted from .357 to 38/40. The gun was new unfired; plans are for Dan Love to engrave it and Turnbull to do a custom finish.
Single action revolvers...yeah yeah, Colts are what they are, but the first centerfire handgun I ever fired was my father's Ruger Flat-Top .357 Blackhawk back in the 1950s, so I've been partial to them ever since. The '50s Flat-Tops (and even the current model Flat-Top .357s) are wonderful "packing pistols."
My personal favorite SA is a 1956-vintage Flat-Top .357 that was completely rebuilt by Dave Clements of Clements Custom Guns as an "homage" to my father's gun. I told Dave to make it the most accurate Flat-Top .357 in the world...all I know it that it is a LOT more accurate than I am! I also kept the '50s vintage plastic "fake stag" grips that were so popular then. Doug Turnbull did the masterful refinish on the gun, Include a spectacular color-casehardening on the frame.
For a .22, and S&W M41...as others have stated, maybe the greatest .22 semiauto ever made. My personal gun is a 1950s vintage M41 I got from a pawn shop in Tampa. S&W did the refinish and it was tuned by Lou Lombardi at Falcon Machining, dubbed by AMERICAN HANDGUNNER as "The King of Rimfires." You've seen this gun in several magazine articles.
Michael B