I am sad to say but I didn't really start getting into them until American Band. I really loved that record so I started to do a deep dive of their music and really fell in love with their stuff, reading Where The Devil Don't Stay only mad me like them more. I have got most of their stuff except their early albums, catalog is so vast and their is so much stuff.
(figured I'd move the conversation here, so folks looking for deals don't get too sick of our DBT talk!)
The first time I heard DBT was on Uncut magazine's
Highway 61 Revisited Revisited CD comp circa 2005/2006.
The first time I sought out and
listened to DBT would have been in 2009, thanks to the line, "It's hard to be a good man listenin' to the Drive-By Truckers," on the song "Officer Down" by Carolyn Mark & NQ Arbuckle, whose joint album was a favourite of mine that year (Carolyn is a local institution around here, and generally pretty beloved across Canada.) I listened to
Southern Rock Opera and
The Dirty South.
The Dirty South stayed with me from then on.
The first time I listened to a new release from DBT was
Go-Go Boots, which I listened to quite a bit ("Used To Be A Cop" remains an all-timer for me) but the only other album I really listened to still was
The Dirty South.
On the strength of my love for the above two albums, I gave
English Oceans a listen upon release but it didn't click with me the way those two did, which may well have been situational circumstance at the time, who knows.
American Band was really the turning point for me. That's when I went ALL-IN. It was that tour where I saw them live for the first time, and it was the lead-up to that show when I finally did a proper deep dive into their catalogue. The next year I got a car and suddenly had a CD player so I started picking up their albums on CD. Within about 6 months I'd grabbed the vast majority of them and was dealt some incredible trauma by life, part of which led to my spending dozens of hours a week in my car, where my listening was probably about 55% DBT, 40% Prince and 5% other. For as much as a lot of other stuff sucked very hard at the time, it was a great way to fast-track a deep knowledge of their catalogue.
TL;DR: It's never too late!
American Band was a great entry point. And regardless of when you became a HEATHAN, you did, and that's what matters!
(Didn't really expect to be sharing my DBT "origin story" today but here we are, I guess!)