If you can measure a person’s character by the quality of his friends, Chuck Prophet is a lucky man.

The San Francisco singer-songwriter plays the Southgate House in Newport Thursday with one of those friends, Kim Richey. Earlier in the day, they will stop by WNKU-FM (89.7), where music director John Patrick once described Prophet as “the coolest guy we’ve ever had in here.”

Testimonials are nice, but the proof is in the music. Prophet’s latest album, “Let Freedom Ring!” is a meditation on our life and times, somewhat inspired by one his heroes.

“It was Hunter S. Thompson who really based his career on the life, death, rebirth and total disappearing of the American dream,” Prophet says. “I was interested in that when I started writing songs for this album. I had the window open, and after about two or three songs, I realized that’s where I was going.”

In addition to his solo projects, Prophet is a trusted collaborator to folks like Richey and Alejandro Escovedo among others. He co-wrote more than half of the songs on Escovedo’s 2010 “Street Songs of Love” and partnered on every one on 2008’s “Real Animal.”

“When we get in a room, we just never run out of things to talk about,” Prophet says of Escovedo. “It’s like touching two jumper cables together. The songs just kind of spill out of that. To Al’s credit, he has the ability to make somebody feel like you’ve known him your whole life.”

Prophet’s whole life hasn’t been spent basking in a cocoon of critical acclaim. He started living the rock ‘n’ roll lifestyle as a teenager, and fell victim to those temptations. But while he struggled with a drug problem, he also made good music with the band Green on Red, an early acolyte of the country punk sound.

“We really took that lifestyle thing as far we could,” he remembers. “We were working with (Memphis musical legend) Jim Dickinson on a record called ‘The Killer Inside Me,’ which kind of split the band, brother vs. brother.

“While we were there, Alex (Chilton of the Box Tops and Big Star) would drop by. ... Big Star was like the Sex Pistols in their own way ... the influence that it had, just like the influence that the Velvet Underground had, Big Star had the same amount of influence.”

Spending time with Dickinson (who died last year) and Chilton (who died this year) certainly influenced Prophet, but cool innately knows cool.

“The thing about Alex is ... he was cool. He didn’t have to say a lot about (his life and music), and he never did a lot of explaining. There was nothing exaggerated at all. He was the coolest (guy) who ever lived.”

Patrick might disagree. “(Prophet) is just cool. You can’t fake cool.”