Origins of the name: "Roger" and "Wilco" ("will comply") are both affirmative expressions in radio talk.
Roger Wilco is also a name of a freeware Windows voice chat program for all those people who don't believe in the keyboard chat feature found in FPS games or flight simulators, or any situation in which sergeant's bark is faster and more convinent than his typing fingers. It's developed by HearMe, and Roger Wilco Team, formerly Resounding Technology, Inc.