Whiskey Riff Song Of The Week: “I’ve Always Been Crazy” By Waylon Jennings

Happy Monday, y’all.

Today, we’re kicking off our Whiskey Riff Song of the Week Series (more like bringing it back), where we’ll bring you a new song every Monday from a variety of different eras in country music.

From oldies, to Y2K, to new releases, and even a few selected by all of you Whiskey Riffers, we want to bring you deep cuts, singles, and a few covers you may not have heard before that you’re definitely gonna want to add to your playlist.

And today, the song of the week is by the one and only Waylon Jennings with his #1 hit “I’ve Always Been Crazy.”

Released in 1978, it was the lead single and title track from his album I’ve Always Been Crazy, eventually peaking at #1 on the U.S. Hot Country Songs chart.

Admitting that being crazy has kept him from going completely insane throughout his life (where he struggled with hard drugs at certain points), it became a defining song of the country outlaw movement in the ’70s due in large part to the fact that Waylon lived every single ounce of the words that he sang. He also had one of the best voices I’ve ever heard in my life.

Authenticity like this is hard to come by these days, but Hoss was as real as they come and it’s why he’s remained a country music legend to this day:

And the studio version:

A beer bottle on a dock



A beer bottle on a dock