Toby Keith's Best Songs: 'Should've Been a Cowboy,' 'Who's That Man'

About The Song

Released in 2003, “Weed With Willie” wasn’t your typical Toby Keith fare. Now, Keith is no stranger to celebrating a good time, but this song tackled a subject not often openly discussed in mainstream country music at the time – marijuana. It wasn’t a pro-pot anthem, mind you, but a lighthearted look at what happens when a straight-laced fella like Keith gets caught up in Willie Nelson’s world, known for its laid-back, hazy charm.

This song likely resonates with folks who remember a time when things were a little simpler. Back when a night out with friends could involve a little good-natured mischief, a shared laugh, and maybe a story or two that gets embellished with each retelling. “Weed With Willie” captures that feeling perfectly, reminding us that sometimes the best nights are the ones that take us by surprise.

So, grab a rocking chair, pour yourself a glass of sweet tea, and settle in for a tale of good times (almost) gone toke.

Video