It wasn’t unreasonable to wonder how Bonnie Raitt could follow up her long-awaited breakthrough on 1989’s Nick of Time. Even Bonnie Raitt wondered.

So, rather than heading to a gala ceremony where she’d win a slew of Grammy Awards, including Album of the Year, Raitt slipped away to work on material that would form a foundation for Luck of the Draw.

“I wrote some of these songs even before I won the Grammys,” she told the New York Times in 1991. “I went away to see if I could write something – so that if I did win, I wouldn’t think that Nick of Time was the only thing I could come up with.”

It wasn’t. Luck of the Draw, which followed on June 25, 1991, spun off a hit single in “Something to Talk About” while selling 2 million more copies than the five-times platinum Nick of Time. More importantly, the material explored deeper emotional places, uncovering harder truths.

“The only real drive I have is to not repeat myself,” Raitt told the Spokesman-Review in 2016. “After this many records, I’ve covered a lot of aspects of [being] brokenhearted and angry and all the juicy themes that make for great soul music, and we’ve covered a lot of musical territory. So for me, the most important thing going into a new record is to come up with a fresh set of ideas, musically and lyrically.”

This time, the theme was longevity. The then-41 year old Raitt had always envisioned a career modeled after sturdy heroes like the late Sippie Wallace – who remained active until her death in 1986 at age 88 – and that was finally within her grasp. But she also understood time brings the inevitable challenges.

“I’m hoping I can be around till I’m 90 singing and playing and reaching people, because I’m [dealing with] meaningful subject matter,” Raitt told the Times. “The great jazz and rhythm-and-blues performers don’t get less adept as they get older. Even if they don’t keep their voices, that can actually make it more poignant. I preferred Sippie Wallace at 88 to the way she sang when she was in her 20s.”

Watch Bonnie Raitt’s ‘Something to Talk About’ Video

Raitt had already come a long way, yet still had something to prove: Could she keep momentum? Still, the sessions themselves – again with Nick of Time producer Don Was – were surprisingly loose, considering what was at stake.

“When you get the right people who really vibe with each other, you don’t have to say much at all,” Raitt told Stereogum in 2016. “It’s all about respecting each other’s artistry. It’s getting out of the way and letting a moment happen.”

Dig deeper into the album, however, and a sense of standing on a creative precipice was reflected in the lyrics, the album’s personal tribute, even in the title itself.

In the original “All at Once,” Raitt admitted: “Why the angels turn their backs on some is just a mystery to me.” The title track attributed life’s inevitable ups and downs to “natural law,” then dedicated the Luck of the Draw to Stevie Ray Vaughan – who’d recently died in a helicopter crash after finally getting his life and career back on track.

“‘Luck of the Draw’ and ‘All at Once’ are kind of a suite of songs about fate,” Raitt told the Associated Press in 1991. “I named the record Luck of the Draw because I’ve been brokenhearted and downhearted in the past about the possibilities of political and emotional and professional renewal. I turn around and see friends of mine, they’re still lonely and brokenhearted. Why did I get through and Stevie not get through? It’s just that life is an amazing bit of fate and luck.”

Nick of Time was also perfectly titled, in its own way. Raitt’s initial promise – she had two gold-selling early albums with 1972’s Give It Up and 1977’s Sweet Forgiveness – had evaporated by the early ’80s. Warner Bros. dropped her, as she descended into addiction. Raitt finally rebounded through therapy, joining Alcoholics Anonymous and then seeing Nick of Time to completion.

Watch Bonnie Raitt’s ‘I Can’t Make You Love Me’ Video

She’d found career success, however, but not love. Well, not yet anyway. “In Nick of Time, I was telling myself what kind of love I wanted and what kind of abuse I wasn’t going to put up with anymore,” Raitt told the Times. “This album examines what it’s like to be in a relationship.”

Raitt married actor Michael O’Keefe in the run-up to Luck of the Draw, though she understood what was at stake there, too. “I had done everything else in my life except this, and it was as romantic as I had hoped,” Raitt added. “Marriage is a very challenging commitment to make. It’s probably the last scary thing you can do in your life and still live.”

By 1999, Raitt had divorced O’Keefe, who cowrote “One Part Be My Lover” with her for Luck of the Draw. That gave Raitt’s devastating, first-take cover of Mike Reid and Allen Shamblin’s “I Can’t Make You Love Me” still more resonance in the years that followed.

“It’s a pretty devastating song to sing more than once,” Raitt told Stereogum, with a laugh. “I didn’t have a rule about it being one take, it’s just that we put so much into making that moment very special that there wasn’t any reason to do it again. Plus, I took me a minute to recover from how sad it was.”

As with so much else on Luck of the Draw, “I Can’t Make You Love Me” came together quickly – but its impact was lasting.

“It’s just hands down the greatest gift I’ve been given to sing it,” Raitt told CBS in 2016. “It’s like holding a space for all of us that have been through that terrible heartbreak, and it’s fresh every night. I don’t care how many times they might’ve seen me sing it. It’s new every time.”