It’s not every day you see two titans of country music step into the same song but in 2002, Alan Jackson and George Strait did just that. Their duet, “Designated Drinker,” isn’t just a fun twist on barroom heartbreak; it’s a slice of country gold. With over 1.5 million views, it’s the kind of track that sneaks up on you and never lets go.

Featured on Jackson’s post-9/11 album Drive, the song arrived at a time when America was craving honesty, humor, and comfort. Though it wasn’t released as a radio single, “Designated Drinker” still hit the Billboard Hot Country Songs chart and quickly became a fan favorite. It plays like a conversation between two old friends because that’s exactly what it is.

The song is part clever wordplay, part emotional truth. It takes the idea of a “designated driver” and flips it; into someone assigned to drown their sorrows instead. The banter between Jackson’s smooth baritone and Strait’s unmistakable twang makes the song feel both playful and a little too real.

If you loved the Jackson-Strait chemistry here, then Jackson’s solo performance of “Where Were You (When the World Stopped Turning)” on the same album shows the other side of that coin; thoughtful, heartfelt, unforgettable.

Alan Jackson – Where Were You (When the World Stopped Turning) [Live]

This ballad, written just days after 9/11, became one of the most important country songs of its era. It’s Jackson at his most vulnerable and resonant—a reminder of why Drive was such a landmark album.

While “Designated Drinker” isn’t always mentioned in mainstream retrospectives, fans know the truth: it’s a hidden gem. It’s the kind of duet that could only come from two legends who didn’t need a hit but gave us one anyway. Jackson and Strait haven’t collaborated much, but when they did, it worked.

Alan Jackson – Drive (Full Album Playlist)