Lilly Winwood Accentuates the Positive, Takes Turn for the Verse

Singer-songwriter Lilly Winwood, who has rock ’n’ roll in her DNA, is also full of surprises. 

The fact that she’s the youngest child of rock icon Steve Winwood isn’t one of them. 

Much has been made about their connection, and what effect the Rock and Roll Hall of Famer — a versatile performer and multi-instrumentalist from England blessed with the soulful voice of Ray Charles — has had musically on his 26-year-old daughter since she left for Nashville at the age of 18. 

In a wide-ranging interview in early August for Rock & Roll Globe, the roots-leaning songstress didn’t shy away from questions about living up to the Winwood name. Or any other subject during an hourlong phone chat from the East Nashville home she owns. Punctually calling at the scheduled morning time, she cheerfully announced, “Hi! This is Lilly!” 

One of her early revelations (at least for me) is that this engaging conversationalist has been an introvert throughout her life, much of which was spent splitting time between the United Kingdom and the United States while raised by an English father and Tennessee mother. 

Yet it appears Winwood, who shared exclamatory opening thoughts (“I’m great! I’m just enjoying some sunshine,” and “I’ve got all the time in the world!”) for this interview, enjoys talking — a lot. And not just because she’s on the verge of releasing her splendid sophomore full-length album, fittingly entitled Talking Walls. Dropping on August 26 as a follow-up to 2021’s Time Well Spent, the self-released record takes on some heavy subjects — drug use, addiction, hard day’s nights and heartbreaks — in a lively manner. 

That tone coincides with the entertaining way Winwood unleashes her own story. Let the unveiling begin. 

Revelation No. 1: Talking Herself Out of Quitting

Winwood was ready to give up on music after feeling “burned out” during the making of her first record and “sitting on a lot of those songs for just so long” while trying to get heard. 

“I didn’t really so much know what I was doing,” she admitted. “Then there’s the whole, the music industry. (laughs) When you’re first starting out … there’s lots of like, ‘Oh, yeah, we would love to put this out but …’ I was just so tired of dancing around that. It took the fun out of the process for me.” 

The fresh face imagined herself “on a pedestal for the world to see. … At times, [it] can be somewhat exhausting, especially for me, considering I’m quite an introvert. … You start to question yourself. …

“I was like, ‘Do I really want to continue doing this? … Am I ready for negative feedback? Am I strong enough to handle what criticisms people might throw at me for these songs or this record?’ On top of that, being an independent artist is a helluva lot of work. (laughs) It’s a lot of doing things with no certain outcome, which can be very scary.” 

Winwood overcame those fears and doubts with encouragement from “the people closest to my life,” including some “positive reinforcement” from her family. And watching two kids dance to her songs during a show in Charleston, South Carolina, was “a source of inspiration because it was like, ‘Wow, my music’s influencing some young girls.’ That’s just a really empowering thought,” she maintained. 

Yet the primary reason Winwood might still be singing and writing songs is “just the fact that I love it so much,” a realization she affirmed after one heart-to-heart talk with herself “about whether or not this is something I wanted. … For as many negative criticisms … there’s always gonna be one person that hears the art you make. And it makes a difference to them.”

So “keeping that in the back of my head,” Winwood reflected, “it would be giving up my dream if I stopped.” 

Revelation No. 2: Psychology, Sociology on the Brain

Though Lilly was born on September 25, 1995, in Nashville (her mother Eugenia Crafton, who married Stephen Lawrence Winwood on January 18, 1987, is a native of Trenton, Tennessee), most of her childhood was spent in the Gloucestershire countryside, light years from the bright sights of London. At age eight, she started playing guitar (“definitely a turning point for me”) but began writing songs at 15 or 16. “That was when I was like, ‘OK, this is the direction I want to take. … I’ve been chasing that dream ever since.” 

Though showing interest in class subjects like psychology and sociology (“any studies of other human beings is just so fascinating,” she declared), Winwood delivered a definitive “Hell, no!” when asked if her bashful country-girl self was a good student. Now she regrets not listening to her parents when they told her, “You’re gonna wish you had paid attention in school.” 

There also was little interest in any activity that required spending extra time after the last bell rang. “As soon as 3 o’clock hit, I was home,” Winwood continued. “It takes a lot for me to come out of my shell. … Group sports [in high school], it’s just very intimidating. I was very sporty, though. … I’m very sporty now.” (laughs) 

She did play a less physical version of basketball in England called netball with no backboard and “a lot of running around,” explained Winwood, whose sporting endeavors nowadays include yoga, running, and tennis. 

Dad’s music certainly scored with Lilly at an early age, though. Her favorite Steve Winwood album is still 2003’s About Time, released when she was only 7. “It has a big Latin influence percussion-wise and … I grew up listening to it,” she recalled. “So I probably know it the most, and my mom wrote a couple songs on the record, too. … It reminds me a lot of my childhood.” 

Lilly heaped praise of her two sisters — eldest Winwood child Mary-Clare Eliot (who married Ben Eliot in 2011) and Eliza (whose upcoming nuptials are in late August) — and 29-year-old brother Cal, all of whom were born in the USA. He’s “a really, really talented percussionist and drummer” who plays “sort of hardcore dance music in the UK,” his little sister boasted. 

After getting COVID-19 for the holidays and missing a chance to see her family in England for Christmas, Lilly is excited to go back and perform at Eliza’s wedding. “We’re back and forth between what song [to sing],” she allowed weeks before the event. 

“My sisters are so talented, too,” Lilly later added. “They’re both singers. They both get really shy performing in front of people but … I hear them sing and I’m like, ‘Why the hell am I singing? You guys are great.’” (laughs)    

Revelation No. 3: In the Presence of a Guitar God 

They all are contributing to the Winwood legacy, though. Before their multitalented dad became a successful solo artist, he built a career in the ’60s with the Spencer Davis Group, Traffic, and Blind Faith, the one-tour-and-done supergroup founded with ex-Cream members Eric Clapton on guitar and Ginger Baker on drums, before bassist Rick Grech joined.

Lilly reported her dad is doing “great” at home in England, working on music “all the time” in his recording studio while keeping “his clocks turning, I think. He loves it.” 

Steve Winwood reunited with Clapton for a highly anticipated U.S. tour in 2009, which I had the pleasure of attending on June 21 in Denver. It had been 40 years since first watching them together on stage, getting floor seats with my older brother John for Blind Faith at the International Amphitheatre in Chicago, on July 27, 1969. I’ve always described that as a life-changing musical event, especially since I learned never again to wear a coat and tie in a crowd of hippies. 

As a youngster, Lilly would “make it a point” to go on the road with her dad, and was in attendance when he and Clapton performed for three nights at Madison Square Garden (February 25, 26 and 28, 2008) a year before that U.S. tour. 

“I just remember seeing New York for the first time,” she recalled. “And it was really cool.”

Summers in her mother’s hometown of Trenton, Tennessee, about a two-and-a-half-hour drive west of Nashville, allowed Lilly to discover the Music City’s best qualities. Playing tunes with her brother and father strengthened a “deep connection” to the place known for its songcraft, reinforcing that yearning to move across the pond for good. 

Though Eugenia “had a bit of worry in her when I was starting out,” her parents backed Lilly’s move to Nashville in 2013, which “was definitely my decision,” she pointed out. “I just felt like I related a lot more to the people I had met here than I did in the UK, especially where I grew up. People a lot of the time assume I grew up in London. I did not. I grew up in the middle of nowhere. Like Middle of Nowhere, UK. And the music scene just really wasn’t a thing.

“It’s so beautiful out there but … when you’re an 18-year-old kid, you’re like, ‘I want to see the rest of the world.’ … There were so many different reasons pulling me here. … I think it was sort of destiny.” 

The Winwood family also did “very normal” things at home (with that recording studio on the property) — dancing, playing music and gathering for big Sunday meals. Asked if it ever became a hangout for famous musicians, an unimpressed Lilly recalled, “Maybe a couple. But I wouldn’t necessarily think of that as a standout thing.” 

AUDIO: Lilly Winwood and Steve Winwood – “Higher Love” 

After years of familial fun, she and Steve recorded his Grammy-winning hit “Higher Love” in 2015 (it also landed in a Hershey’s commercial), then toured together in 2017-18. 

Going on the road again as a father-daughter act remains a possibility, though Lilly acknowledged, “Touring is just very tricky these days because of COVID. Like, hopefully, and I’m sure he thinks the same, hopefully. But … you just don’t know. It’s hard to make any promises these days.” 

The best piece of advice Lilly said she received from him was what he called the Five P’s — practice, practice, practice, practice, practice. “You’ve got to put in the hours. That’s how you really see a difference in anything,” realized the musical sponge, who recently began soaking up lessons on the “fascinating” pedal steel. “It’s very rarely that you get these prodigies that come out of the womb ripping guitar solos.” 

Unless he’s a wunderkind known as “Little Stevie” Winwood, who left school to become the Spencer Davis Group’s 15-year-old lead singer. In his Clapton autobiography, the guitarist wrote that when he first saw the teen dream perform, “Musically, he was like an old man in a boy’s skin.” 

Once an up-and-comer herself, who started writing songs at the age of “Little Stevie,” Lilly is filled with admiration while discussing her influential dad, now 74: “He opened a lot of doors for me in the sense that he was like, ‘Hey, come on the road with me. Just open a few shows. See how you like it.’ And that’s huge. … [He] truly solidified in my head that I want to do this.” 

Following in his footsteps is no cause for concern, Winwood concluded: “It’s very much my journey. I’m very grateful for my parents for giving me the chance to make it my own journey and to have the freedom that I do. I feel zero pressure, apart from my own conscience.” (laughs)

Revelation No. 4: Who Sounds Like a Valley Girl? 

Becoming a full-time Nashvillian wasn’t a smooth transition, though. 

Winwood released her first EP (Silver Stage) in 2017 and worked with cool local musicians like Boo Ray (covering “Islands in the Stream”) and Allen Thompson, whose Lady Couch bandmate Keshia Bailey joined him on stage to celebrate Winwood’s 26th birthday during her AmericanaFest showcase last September. But small nibbles at success while getting her music career off the ground in East Nashville left Winwood hungry for more. 

To make ends meet, she became a bartender and waitress. Though it probably wasn’t fun (or funny) then, the evolving Englishwoman developed what she called a “fake” American accent to ward off trite queries from customers. 

“I have a very strange accent. All the time, people think I’m from Australia,” she divulged, comparing herself to a British-American adventurer on the HBO series Edge of the Earth. “He has the weirdest accent, which is like mine, like a mix. You cannot pinpoint it. … I know certain words that people just do not understand. And I’m so sick of people being like, ‘What? What?’ Or wanting me to repeat myself.”

She began working on Americanized ways to say “water,” “trashcan,” and “bathroom,” but got grilled or ridiculed for her pronunciations. Even Winwood’s boyfriend mimicked her with an over-the-top British inflection that keeps rising, to which she retorted, “You sound like a pirate.” 

Showing her vocal versatility by transforming from British to American in seconds, Winwood gave a spot-on impersonation of a voice many U.S. residents outside California love to hate. “I feel like I sound like a bit of a Valley Girl if I turn it on. ‘Hey guys, how’s it going? Like, you want some water?’”

Revelation No. 5: Sobering Thoughts

While that was on the lighter side of adjusting to Nashville’s nightlife, Winwood also has dealt with darker moments. 

In 2020, she decided to get sober after bouts with “drinking and substance abuse in general,” Winwood disclosed. “Like anything else you really can be addicted to. … Sobriety is a very broad term. And I think that applies to a lot of different things.” 

Politely declining to provide details regarding the extent of her problem and whether it involved getting outside treatment, she emphasized that relying on the “support of friends and family … was really important … the No. 1 thing to do. … But at the end of the day, if you’re planning on getting sober, it’s really up to you.” 

Her sobriety is going “really well. Thank you for asking,” Winwood asserted. One reason for her decision was “just being my overall health. … I’ve seen a life of what it’s like to be sober and what a life it’s like to not be sober. I prefer the one that keeps me healthy.” 

Abstinence also gave her a “whole new view on songwriting,” she expressed in her bio, and a wealth of material that appears on Talking Walls. 

“It comes from a place of … relying on songwriting to get some certain feelings out in a healthy way,” Winwood specified in our interview. “Whereas before, I wouldn’t take the time to sit down to songwrite. … I would throw up words and put down on paper just so it was always a bit random. … It didn’t feel as sincere as the songs that I have written since I’ve been sober feel to me.”

Revelation No. 6: There’s More to Idaho Than Fly Fishing 

When the global pandemic hit in 2020 and all touring stopped, Winwood became a waitress in a Nashville restaurant operated by M Street. Any spare time was spent writing songs (or snippets of them), even during working hours that ended in the AM.

“I would write down all these ideas on scrap pieces of paper and throw them into my apron,” said Winwood, whose album’s nine songs she wrote from April to September 2020. “Then I would get home and I would uncrinkle them and try and piece a song together. I think the majority of my songwriting happened between the hours of 2 [and] 5 in the morning.” (laughs) 

Tough subjects appear in songs like “Good Old Days” (“Found that the good wasn’t that great after all”), “Long Haul” (“Why the hell would you even want anything to do with this mess”) and “A Paper Trail of Broken Hearts” (“You said trust me take two of these / Felt my skin turn inside out”). Yet most of the material is made quite pleasing to the ear through Winwood’s band at Trace Horse Recording Studio, along with her own fluid vocals and an acoustic guitar adding a refined, elegant touch. 

VIDEO: Lilly Winwood – Brighter Days

“A Paper Trail of Broken Hearts” includes guitarist Laur Joamets’ Tom Petty-like intro; Philippe Bronchtein’s weepy pedal steel elevates “Brighter Days” and “Long Haul”; and the swampy slide guitar on “Airplane” smooths the song’s rough lyrical edges that include the album’s grimmest line — “Now he’s traded heroin for a ghost that lives within.”

“When I first wrote that song, it had a very somber feel to it. … I was kind of like, ‘We can talk about [addiction] and [make] it not so gloomy,’” asserted Winwood, who successfully guided a team of musicians, and engineers Scottie Prudhoe and Preston Cochran, all of whom “brought their very own spin to this record.” Spitballing ideas around a table that led to six or seven takes, Winwood said, “It was just the most comfortable I have ever felt in a studio.” She thought to herself, “Who needs a producer?”

With players also including Steo Britton (bass), Daniel Kozlowski (drums / percussion) and Chip Colon (keyboards) in such high demand, Winwood is taking a more intimate approach on the road to support Talking Walls. Opening shows for Jackie Greene through August and Todd Snider in September, she believes performing solo will allow her to “feel a lot more of a connection to the audience when I’m able to go up there fully as myself and portray my songs the way I wrote them, which was me and my voice and a guitar.” There’s also hope those unsettling lyrics will get their attention. 

That might mean the album’s rowdiest cut — “Idastoned,” driven by a honky-tonk piano —misses the setlist. At least until a keyboardist like Colon (who “was banging on the keys with his fists” in the studio take they loved and used, according to Winwood) is available to play this ode to the wonders of nature (and getting high). It just might become Idaho’s state song. 

Calling it a “goofy little number” written after an intended fly-fishing trip in Idaho, Winwood put that outdoors activity aside and “figured out quickly that I was just a whole lot better getting stoned and going on a hike. … Being out in all that beauty, you’d expect somebody to come up with some profound piece of poetry, but I came up with that.” 

These days, though, Winwood gets high on life. She considers an invitation to open for Brett Dennen last year her “aha moment,” saying, “I was like, ‘Holy shit!’ … That’s something I’ve achieved completely on my own.” 

Progressing so much since 2020, Winwood proclaimed, “I’ve come to terms with the fact that I’m just so happy with where my career is right now. I’m able to tour with these amazing musicians. And get my music out to people, make money doing it … and all these doors are opening for new experiences. 

“I’m just able to create art at a pace that’s comfortable for me and where I have full control over it, too. … I really do believe that I’ve made it.”

Whether she’s running into family, friends, fans — or walls for that matter — Lilly Winwood should be talking the talk for a while — in whatever accent she chooses. 

VIDEO: Lilly Winwood “Keep It Spinning”

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Michael Bialas

Michael Bialas is a Colorado-based journalist and photographer who enjoys covering entertainment and sports for a number of online publications. Follow him on Twitter: @mjbialas

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