3. "I Ain't Living Long Like This"
Written by Rodney Crowell and recorded by Emmylou Harris, this live fast, die whenever anthem took on new energy when Jennings wrapped his rough-hewn baritone around it. While he may not have done exactly everything the lyrics talk about — although he did run afoul of the law in 1977 for cocaine possession — Jennings sang it with such believability that one would believe he was a lifelong jailbird. The song further cemented his image as a badass and also gave him his 11th Number One country single. Today, "I Ain't Living Long Like This" remains a honky-tonk staple with artists from Justin Moore to Andy Griggs offering interpretations. Most recently, Vince Gill and Grand Ole Opry favorite Chris Janson performed it together on the Opry stage.