"ALL THESE SONGS are about death," announced Vic Chesnutt during a recent set in New York. And my god, are they ever. Much of Chesnutt's material is viciously difficult. A vivid tangle of depression, confession, fear, and lament, he is a constant reminder of Buddha's First Noble Truth: Life is suffering.

And though confrontation of these feelings often brings reward, I was still a bit surprised when Chesnutt appeared on the other end of the phone line bright, gregarious, and cracking jokes. (Surely artists' personalities are not bound to be accurate reflections of their craft, but few are as unwaveringly solemn as Chesnutt.) He spoke from his home in Athens, Georgia, on a quick break before heading west. Things so far have gone exceedingly well.

"Best tour ever!" Chesnutt exclaimed. "I've become fucking good for once in my life." This from a man who's been performing around the world for the past two decades.

Although the statement seems a bit tongue-in-cheek, Chesnutt insists it's not. What is certain, however, is that the artist finds himself in the midst of a creative renaissance. The genesis? Friends.

This fall Chesnutt released two albums; the first, At the Cut, is a rich affair with a band featuring members of Godspeed You! Black Emperor, Thee Silver Mt. Zion, and Fugazi guitarist Guy Picciotto. On the other hand Skitter on Take-Off, produced by the seminal Jonathan Richman (performing on Wednesday, December 2, at the Aladdin), is live, simple, and mostly solo. They are very different documents.

At the Cut came at the behest of Chesnutt's friend, filmmaker Jem Cohen, who assembled the intriguing backing band. It's their second album together. According to Chesnutt, Cohen hated his last two albums and said he wanted "to make a good Vic Chesnutt record." The intense, brooding dynamics of the players are given plenty of room to work within Chesnutt's stark, straightforward compositions, but they never overshadow the importance or immediacy of the frontman's raspy voice. The emotional stakes were raised, just as Cohen had conceived. "It was a brilliant idea," said Chesnutt. "One of the best things to ever happen to me."

Another one of those watershed moments was Chesnutt's meeting of Richman some 20 years ago. "One of the most important things I've learned from Jonathan is to have a comfort level with my own talent," Chesnutt explained. "It was through Jonathan's encouragement to know you are an artist and what you're doing is worthwhile. Not just worthwhile—but revolutionary."

The wide-eyed, sunny Richman might seem a strange pair with the acerbic Chesnutt, but that difference of perspective is precisely why it works. And just as Cohen's plans came as a response to earlier work, so did Richman's. He hated the big, full-band studio sound, seeking instead Chesnutt's raw, up-close, and un-adorned approach.

Two weeks after recording At the Cut, Chesnutt headed to Richman's San Francisco studio with a handful of songs written just days before. Much like its sound, the content of Skitter is the polar opposite of At the Cut. Where the first recording is "very personal," Chesnutt explains Skitter is almost "all fiction."

The torrent of contrasting work has been artistically freeing and fulfilling for Chesnutt, and after many collaborations he feels a special kind of synch with his current band. Creatively, Chesnutt couldn't be happier—so much so he feels he could change the minds of his doubters. "I know a lot of people know who I am," he said. "I've been around for 20 years, and they think I suck. Well, this will be the show to see."