On Sunday, September 20, 2009, this episode of "Pushing Daisies" won an Emmy Award for Outstanding Art Direction For A Single-Camera Series.
The title is a pun based on the expression "Win Some Lose Some".
When going undercover, Ned dresses like a cowboy, complete with hat, tie, and boots. In real life, Lee Pace was born in Oklahoma but grew up in Spring, Texas.
The episode won 2 Emmy Awards for Outstanding Makeup for a Single Camera Series (Non-prosthetic) and Outstanding Art Direction for a Single Camera Series.