“Janis called me direct, herself,” regales Bobby Womack down a scratchy telephone line from his home in Los Angeles. “She said, ‘I want to record one of your songs, ‘cause it seems like everybody else is singin’ your songs.”

It was 1970, on the way to a recording session with the late Janis Joplin, in his new Mercedes-Benz. Joplin was in the midst of recording what would later become Pearl, her most acclaimed work, when she came out to meet Womack in the car. “She starts beating on the dash singin’, ‘Dear lord won’t you buy me a Mercedes-Benz’,” he recalls. And the rest is history.

The tale is one of thousands in the career of Bobby Womack, a creative journey that spans five decades. Elvis Presley, Ray Charles, Aretha Franklin, The Rolling Stones – the singer-songwriter’s resume reads like an encyclopaedia of popular music. Cutting his teeth as the lead singer of family R&B group The Valentinos, Womack lent his talents to countless acts throughout the 60s, 70s and 80s, nurturing his own career as a recording artist at the same time.

At home for a rare break before heading to Australia later this month, Womack says the hotel life is beginning to take its toll after 50 years on the road. “I’m at home now, which is a place I never get to be. All this jumping off and runnin’ through airports, man, it’s takin’ the breath out of me,” he says.

But while it’s hard sometimes, the hotel life is a good kind of monotony, and the 69-year-old has lost none of the zeal that earned him induction into the Rock & Roll Hall of Fame in 2010. “The thing that remains fun is walking onstage and getting in the wings. I never take my audience for granted. When they call my name and the people go up, I go up. I’m in another world,” he says with the kind of enthusiasm that’s rare for someone in an industry that leaves so many of its stalwarts jaded.

Over the course of our conversation, Womack recalls some of his most documented adventures, confessing he was “no saint” in his youth. He was with Janis Joplin on the night she died in 1970 and says that even with the passing of time, he’s left scarred. “I was the last person that saw her,” he says, thinking back to the night Joplin passed. “I remember her sayin’, ‘Bobby I’m waiting on somebody’.”

Shortly after leaving her apartment, Womack received a phone call from Joplin’s producer and he was told the tragic news. “I was like, ‘Are you serious? I Just left her’,” Womack recalls. “He said, ‘She had your new album on the turntable…’ It was weird, that freaked me out for a long time.”

After marrying the widow of mentor and friend Sam Cooke shortly after his death in 1965, Womack felt ostracised from the music community, despite his commercial and critical success. It is a feeling he has only been able to shake in recent years, since his collaboration with Damon Albarn (of Gorillaz and Blur fame), which introduced his work to a new generation of music fans.

Womack is grateful for the commercial rebirth, but remains pensive about whether his contemporaries would appreciate the new direction. “I’m still growing. If someone had told me 10 years ago, ‘this will be you’, I would have said ‘no, no, no’. Man, I don’t know if the Sam Cookes or the James Browns would like it. I don’t know. But it feels good to me.”

A man willing to follow his instincts and take risks, Bobby Womack has achieved the longevity that eluded most of his peers. And according to the man himself, the formula is pretty simple. “You’ve gotta keep reaching, if you wanna keep living.”

Bobby Womack is playing at Vivid LIVE at the Sydney Opera House on May 24 and 25.