“If retirement means spending your days doing what you love to do, then I’ve been retired my whole career,” Lovett told the Aspen Daily News on Monday.

Tonight at the Belly Up, Lyle Lovett will have arriven. He will not have arrived, but arriven. The story goes, it was Nashville, 1993. Lyle and His Large Band, busy rehearsing for a forthcoming tour, were waiting for band member Francine Reed to show up. Finally, Ms. Reed bursts through the door, announcing: “I have arriven!” The phrase stuck and is uttered to this day among the band.

Lovett is not new to Aspen. He has arriven plenty of times before. Former Pitkin County Sheriff Bob Braudis remembers when he first met the singer-songwriter from Klein, Texas.

“The night of the Howling Wolf. It was the early ’90s. Lyle was playing at the Wolf, and through Hunter [Thompson], already a friend of Lyle’s, that’s how we met. I drove to the show with Hunter and Lyle played until three in the morning. He left with the prettiest girl. It was a wild night, lots of Freak Power.”

Another time, Braudis recalls the fate of Lovett’s 1971 Cadillac Eldorado. “Hunter sold the car to Lyle, and then one night while Lyle was in town, Hunter crashed it into the St. Regis. There was sixteen thousand dollars worth of damage. We named the car Geronimo’s Cadillac.”

Lovett recalls Thompson offering to sell him the vehicle for $2,000, backstage of the Wheeler. 

“I said to my manager, ‘Pay him.’ Hunter met me at the Texaco on 82 and it was pitch black. He arrived with a Maglite and started selling the thing to me like he was a used car salesman. There was even a case of beer in the trunk,” Lovett said Monday in a telephone interview.

Turns out, the car never belonged to Thompson. “But we drove it to our next stop on the tour, Salt Lake City, and then one of my band members drove it back to Nashville,” Lovett said. “We never found out whose car it really was.” Where’s the car now? “I’m pretty sure Juan [Hunter’s son] now has it.”

Lovett loves Aspen. “It’s such a great community. Forward, open-minded, artistic, it’s always a pleasure to return and see old friends and make new ones.” The first time he was in town was 1987 when he opened for Bonnie Raitt in what the Belly Up used to be: the Double Diamond. “It’s such a great room, so many great memories, small and intimate.”

This time around, he will be joined for the sold-out performance by four other musicians forming Lyle Lovett and His Acoustic Group. Speaking of his music: “I just try to write [music] that means something to me. Music is an emotional medium and can be so powerful. It can coexist with anything else someone might be doing. Instead of putting life on hold, music can be a part of life. The nicest compliment from someone regarding my music is when they say ‘the first time I heard that song of yours, I was doing such and such.’ If my music can remind someone of their own life, I’ve succeeded.”

Braudis through the years has befriended plenty of musicians to swing through Aspen. To him, Lovett was different. “Lyle is the real deal. There’s no fake with Lyle. Through his music, he emotes.”

In fact, Lovett is a rare breed in Aspen. He’s also an honorary deputy sheriff. While still sheriff, Braudis made sure of that. There aren’t many deputy sheriffs, and Lovett is one of them. So is another friend: fellow Texan and Aspenite Lance Armstrong. Sheriff Joe DiSalvo bestowed Armstrong with that honor, Armstrong reported on his podcast.

So what we have here is a musician that takes some getting to know. Lovett is layered. For those that don’t know his music, the immediate assumption is that he’s country. Which is true, to a point, but his canon brims with musical influences from a wide variety of genres. More accurate perhaps: A balladeer with a Texas twang; a troubadour delivering clever, literate lyricism. A melodic voice matched by a kick-ass band tighter than an otter’s pocket.

Since the Night of the Howling Wolf, Lovett has recorded 13 albums, released 25 singles, won four Grammys, acted in Robert Altman pictures and briefly was married to Julia Roberts. His family lost the farm, but his success enabled Lovett to piece it all back together. At this stage in the 62-year-old’s life and career, it’s clear: Lovett has arriven. 

“My goal though was just to do well enough so that I could keep doing it. I am so grateful to the audience for still showing up and If I were to retire, I still would want to play music,” he said. “If retirement means spending your days doing what you love to do, then I’ve been retired my whole career.”

But that sure doesn’t meet he’s lost his inner freak. Hunter and Bob would never let that happen.