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Credit Richard Burbridge for The New York Times
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One evening last fall, Teddy Thompson stepped onto the stage at the Purple Crayon, a cultural center in Hastings-on-Hudson, not far from New York City. The venue regularly attracts established pop-folk singers, the kind embraced by the public-radio-listening, Subaru-driving locals; Thompson loosely falls into that category, although he has the louche glamour of a heartbreaker, as well as the reputation (“I haven’t been invited on the Lilith tour,” he once dryly pointed out in an interview). Tall, fair, lean and British, he sang that night, with what one admiring critic has called his “keening tenor,” a series of songs about failed relationships in which Thompson, single at 38, was usually the bad actor: “I was born with a love disease/It’s known as chronic hard-to-please.”

On more than one song, he stumbled over his lyrics, stopping altogether to start again; but that only provided him an opportunity to charm the audience with a diffident kind of humor. “Here’s the thing,” Thompson said. “Are you going to sit at home and listen to your own records to prepare? Feels stupid.” And then he sang, with clarion, soaring tones that defied the pretense of aloofness and justified why The New York Times has called him “one of the most gifted singer-songwriters of his generation.” Thompson delivered a performance that seemed capable of collapsing from total negligence or veering toward greatness, which layered onto the set an element of suspense.

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Songs From “Home”

Four tracks from the Thompson family album, including the exclusive release of “That’s Enough.”

As he neared the end of the show, Thompson announced, “This is a song I wrote for my mother.”

The audience immediately hushed. Some might have even been there because they were fans of his mother, the singer Linda Thompson, and his father, the legendary guitarist and songwriter Richard Thompson, who began their musical collaboration in 1974 with “I Want to See the Bright Lights Tonight,” an album considered a folk-rock masterpiece. Eight years later, in 1982, they released the album “Shoot Out the Lights,” which Rolling Stone deemed one of the 10 best of the decade. On it, Richard plays guitar with an exquisitely controlled rage, and Linda, with her clear alto, sings spare, timeless lyrics that catalog the implosions of their dying marriage. The couple separated that same year, when Teddy was almost 7.

The song Teddy Thompson set out to sing, “Home,” is one of his strongest, full of small details iconic and intimate: “Can’t sleep in too late/Bed’s got to be made/Breakfast table’s laid/Eat, you’ll waste away.” Offering a voyeuristic glimpse of home life, the lyrics lulled the audience until Thompson reached the bridge. “Fall right back/Into the family embrace,” he tried singing, but he played the wrong chord. He tried it once more but again misfired. “It’s a very difficult bridge; that is something I should have learned,” he muttered, suddenly unguarded, genuinely apologetic. He looked up at the ceiling as he tried to work it out, this small musical bit about something so primal: “Family embray . . . embray . . . family embrace.” He paused. “No, that’s not quite it,” he said one last time. Finally he moved on, leaving the distinct impression that whatever his relationship to that family embrace, he was still struggling with it.

Over the past 15 years, Teddy Thompson has sung and written songs about love, about sloth, about partying, about murder. On Nov. 18, his latest project will be released, a collaborative effort called “Family,” which both directly engages that topic and tries to engineer, through harmonies and technology and talent, a kind of musical reunion. His mother and father each contribute songs and music, as does his nephew, Zak Hobbs; his sister Kami Thompson; her husband, James Walbourne; and Richard’s son from his second marriage, Jack Thompson. “At first I just thought it would be something fun and easy,” said Teddy, who eventually realized his motivations were more complicated: “I definitely was trying to repair some kind of damage.”

Or possibly inflict some, Kami, also a songwriter, later suggested. “The whole album,” she said, “is like a family songwriting competition — it’s a bloody nightmare. I mean, what could possibly go wrong?”

A year ago this month, Thompson flew from New York, where he lives, to Los Angeles, to work on the album with his father. When we met for coffee before the trip, he explained that he never doubted his father’s willing cooperation on the family album. “I just knew he couldn’t say no,” he said. “Because he kind of owes me in a way.”

Now 65, Richard Thompson lives in Pacific Palisades in a cottage with a small pool in back, as well as a modest guesthouse with an island theme — a surfboard lodged in the rafters, sofa cushions with a palm-frond pattern, a mural of Polynesian bathing beauties smiling down from the wall. Teddy briefly lived in the guesthouse when he was first starting out in the music business, but now Richard uses it as a recording studio. As they set up, Richard and Teddy untangled cords and fiddled with equipment. Richard worked barefoot and wore black cargo pants; Teddy, who has his mother’s expensive tastes, wore skinny jeans. They talked about some sounds they were going to try out later that day, including the hurdy-gurdy, of which Richard is a fan. “It’s very easy to play,” Richard said. “It’s simply hard to play well.”

“Which one will you be doing?” Teddy asked.

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Richard Thompson, circa 1993-4. Credit Richard Burbridge

Richard had already written two songs for Teddy’s album, but that morning, they were listening to a song Kami wrote, “Careful,” a country-pop tune with ’80s overtones, onto which Richard was going to overdub some guitar. From the outset, Teddy had imagined the process of making the album as a game of telephone: Each would electronically forward the songs they wrote to the others, who would remotely layer on vocals and guitars with Teddy’s guidance.

The system was not just the easiest one, but probably the only one possible for the project. No one seemed interested in testing Linda and Richard’s current polite rapport by asking them to record in the same room, especially given the memories that arrangement would evoke of their last, cataclysmic collaboration. Richard and Linda recorded “Shoot Out the Lights” when Linda was pregnant with Kami, their third child. Richard had written lyrics that portended the relationship’s end: “This grindstone’s wearing me/Your claws are tearing me.” Shortly after they finished the album, the couple split, and Richard paired up with a club manager named Nancy Covey. The couple was compelled, however, to plow their way through a tour, with Linda tremulously singing her way through songs about rejection and loss (“I wish I could please you tonight/But my medicine just won’t come right”). The emotional pitch of their performances made for heart-rending vocals and memorable visuals: Midway through one performance in Providence, Linda kicked Richard in the shins; at others, she tripped him.

Following that tour, Richard remained on the road, trying to make a living, and eventually moved to Los Angeles with Covey, to whom he is still married; Linda stayed in London with Teddy, Kami and her oldest child, Muna (the only one of the three who does not sing professionally). Linda remarried to a successful talent agent, Steve Kenis, and Teddy, a shy, sensitive child, saw little of his father until he was 18. As soon as he finished high school, he left London and moved into the guesthouse, determined to begin his own career as a musician. The decision seemed fraught, and yet as Teddy sees it, the choice was almost inevitable. “When your dad has left you, and you want to be closer to him, and that’s what he does, of course you’re going to want to do that,” he told me. “It’s not rocket science.” His extended circle of friends includes a compatriot crew of second-generation musicians, many of whose parents divorced or spent extensive time on the road: Sean Lennon (son of John), Rufus Wainwright (son of Loudon Wainwright III and Kate McGarrigle) and Harper Simon (son of Paul).

Thompson released his debut album in 2000 with a lucrative record deal and since then has made five others, the most recent of which was “Bella,” inspired by an ex-girlfriend, in 2011. At the time, one critic called him “too fantastic for his own good” — intimating that someone that literate and understated would probably never find the kind of mass audience necessary for profitability in the industry today. The prediction was accurate. Following the poor record sales of “Bella,” Thompson’s label, Verve, did not renew his contract. Around the same time, Thompson’s most serious romantic relationship ended. Adrift personally and professionally, uninspired to do much songwriting of his own, he turned to his family: He would lean on them for his next album, for support, for collaboration, for some kind of magical undoing of the fissures — “the things that happened when I was a kid” — he held partially accountable for his current state of affairs.

At the guesthouse, Teddy and Richard eventually settled down to work. The conversation was, at times, painfully polite; Richard’s innate British reserve seemed to infect his son. At one point, Teddy tried to explain to Richard when he should play on Kami’s song, but he was too restrained to make himself clear. “That’s the main bit,” he said, meaning, Don’t play. His father played over that same section once or twice, until Teddy said, “Those are the main vocals, so you don’t need to do anything fancy there.” Teddy was in charge but still slightly cowed. They started again, and this time Richard waited for the right moment, playing a twangy counterpoint that gave the song more texture. At last they were pleased, but when they looked at the monitor, they realized the song hadn’t been recorded. “Oh, dear,” Teddy said. “It doesn’t matter,” his father replied.

Growing up, Teddy felt that music was a language through which he could make sense of his father, if only he listened closely enough. “That was a way I could understand him, because he wasn’t around very much,” he said. He played his father’s albums over and over and pored over the lyrics to his songs. “Music was a very useful tool for me to have,” he said. “Both his and my mum’s, to see a little more deeply who they are, as well as who they were.”

When Thompson received his first record deal, he asked his father to overdub a guitar track for the song “Days in the Park.” The song explicitly touches on the resentments an adult child still feels about his father’s longstanding absence: “I bet you think it’s over/The misery is gone/Turn your back and promise/Days in the park.” Richard complied, weaving in a kind of response that quietly reflects his son’s pain, without overshadowing it, and seems to imply his own. They never spoke about the lyrics, and Teddy considers the musical conversation the most substantive one they have had on the topic.

I had intended to ask Richard about that song the day I met him and Teddy in Los Angeles, but the contagion of reticence in the room made it almost impossible, and I eventually followed up by phone. “I think it was understood what the song was about, what a hard time it was for Teddy and me,” Richard said. “Perhaps there’s catharsis in it for Teddy, and that’s great — but the main point is it’s a good song.”

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Linda and Richard Thompson in Sheffield in the early ’80s. Credit Photograph from Linda Thompson

That morning in the bungalow, Richard and Teddy eventually moved on from Kami’s contribution and went over the vocals for “One Life at a Time,” one of two songs Richard contributed to the album. He belted the lyrics, expressing, in his tone, the hint of a sneer: “One life at a time/One life at a time/If you’re busy living your life/You won’t be living mine.” And later: “Sometimes it’s hard to say/What you got to say anyway/I’m gonna have to say/That I’m not thrilled about you.”

Teddy was under the impression that the song was vaguely about politics. But given the family dynamics, it was hard not to read into the lyrics that same sense of familial suffocation that drives some of Richard’s most famous, and infamous, lines. “The End of the Rainbow,” written not long after Muna was born, captures a new father’s bleak panic: “I feel for you, you little horror/Safe at your mother’s breast/No lucky break for you around the corner/'Cause your father is a bully/And he thinks that you’re a pest.”

The Thompsons’ songs are generally loaded with enough honesty to ring true but also enough poetic license to defend against literal interpretation. None of it makes for typical family conversation. But as Joe Boyd, a producer who has worked with many of the Thompsons put it, “The music wouldn’t be as interesting if they were normal people.”

For all their dexterous songwriting, Teddy, Richard and Linda have an array of vocal quirks that seem to announce the challenge of simply uttering language. Richard has a slight stutter; Teddy has been known to go entirely blank on lyrics onstage; and Linda, during her pregnancy with Muna, developed what is known as spasmodic dysphonia, a condition sensitive to stress in which the vocal cords periodically seize up. She managed to release a solo album in 1985, which fared poorly, then stopped recording her own albums until Teddy released his own, in 2000.

“I think there was something about watching me do it that either got her interested again or got her juices flowing,” Teddy said. “Or she wanted me to be proud of her and show me who she was.” Writing many of her songs with Teddy, Linda released “Fashionably Late” in 2002, an album full of haunting folk ballads about murder, loss and longing.

Writing by email — dysphonia makes talking on the phone a challenge — Linda offered a competing theory. “No, my mother’s death was the catalyst for that album,” she wrote. “Teddy is a teensy bit more narcissistic than I thought.”

Her comment was a rare bit of criticism from an unusually doting mother. “Teddy is the love of my life,” Linda wrote me at one point, “the only man I have ever loved unconditionally. That is probably quite tough for him, but what are you going to do?” Partly because of that closeness, the making of “Fashionably Late” was hard on their relationship. Linda’s voice seized up in take after take, and Teddy grew impatient. “It was almost like I was taking my dad’s place in the studio,” he told me. “She associates music with a very traumatic time in her life, and being back in the studio was very difficult for her.” Linda wrote: “It’s difficult for him to watch me having a hard time. He is, of course, the one musician in the world I most want to impress.”

While working with Teddy on “Family,” Linda wanted to record another take for one of her songs, worrying that her voice sounded too weak. But Teddy thought that fragile quality worked with its tone. The way they handled it, says Linda’s grandson, Zak Hobbs, was “traditionally British — we didn’t really say anything until he got back to New York, and then they emailed back and forth about it.” Teddy compromised, stitching together snippets from her various takes.

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Teddy Thompson, right, with his parents, Richard and Linda Thompson, in the late 1990s. Credit From Linda Thompson

With all the old family rivalries and tensions at play, Teddy felt that the physical space between him and his mother while they worked ultimately helped. “It was good we weren’t in the same room,” he suggested to his mother one afternoon, over tea in the lobby of the Marlton Hotel on Eighth Street. Linda, in town visiting, wore an old concert T-shirt of Rufus Wainwright’s — she was close to his mother, Kate McGarrigle — and a massive antique diamond ring, the likes of which she now sometimes sells as a part-time dealer of fine jewels and art.

Teddy reassured her that he thought distance helped his working relationship with his father, as well. “He sent me all these things he added after he’d heard the rough mix, and I didn’t use any of that,” he said. “I thought it was rubbish — it didn’t make the song any better at all. And it would have been different if we had been in the same room at the same time, because of the different dynamic. I would have bowed to his expertise and experience and regretted it.” He paused for a moment. “All I’m saying is that not being anywhere near each other is fantastic for our working relationship.”

Only Kami Thompson, Teddy’s younger sister, 32, admitted that she would have preferred to skip this particular project of Teddy’s. “I did say, ‘Could I be like that one Osbourne who’s not on the show, whose name no one knows?’ ” she told me. The prospect of collaborating on music with her nuclear family evoked a strong flight response, as if they were the last people with whom she might share such an intimate experience. “It’s quite a personal thing, music — it was enough to slightly spook me,” she said. Although each of the family members (Muna excepted) has played and performed with one another on occasion, she was also unsure of what to expect, because they were hardly a family that grew up regularly playing music together. Linda’s dysphonia rendered her songless for most of Kami’s childhood, and Kami did not start singing in any dedicated way until long after Teddy left home. “It was a distinctly unmusical household,” she said. “I grew up like everyone else, listening to albums in my bedroom that my parents didn’t like.”

While working a day job in the entertainment industry, Kami did eventually release a solo album; she now performs full time, singing vocals alongside her husband, James, a sought-after lead guitarist (their band, the Rails, released its first album, “Fair Warning,” this past spring). Unlike Teddy, she and James have tried to establish themselves as musicians apart from her family history; but she was all for her brother’s decision to delve into it directly and ultimately wanted to support — or indulge — him along the way. “I think it’s hilarious that he’s gone all New Age, let’s-talk-about-it,” she said. “It’s great to see someone you love processing things.”

Kami was most apprehensive about the one-upsmanship that hearing one another’s work might inspire. But in the end, it was her song that caused anxiety: After hearing Kami’s “Careful,” Linda went back to rework one of her own songs, convinced that it did not measure up. “I told my producer, Ed Haber, ‘No pressure here — but my song has to be the best one,’ ” Linda wrote.

The strain of competition between musicians and their children goes deeper than just ego, suggested Rufus Wainwright, a close friend of Teddy’s (his own fractured family released a reunion album, “The McGarrigle Hour,” in 1998). “You’re stepping into a world in which there’s this inherent tension between age and beauty,” said Wainwright, whose relationship with his own father has had strains. “And it could get tricky in terms of — Oh, it’s all about death; it’s all about our fathers. They are next in line. And they don’t want to go.”

Teddy was running up against the deadline set by his new label, Concord Music Group, when in May he recorded the final song — called “Family” — for the album. Zak plays guitar along with him on it, and his mother delicately lends grace to a mournful harmony. Against a 3/4 meter, he outlines, somewhat starkly, the shape of his life: the beautiful sisters on either side, the great musician father, the singer mother, the struggles he has had to move forward, to find his way out from being “betwixt and between/Sean Lennon, you know what I mean.” And he sings about wanting to forge a way forward with a family of his own: “But you gotta know how to choose/happiness over the blues/ light over dark, willing to start something new.”

He procrastinated for months before writing the song, listening to everyone else’s first. When he and I first met a year ago, he passed this off as sheer laziness: “I’m not a very good self-starter,” he said. But as the release date for the album grew nearer, he acknowledged he was putting it off for the same reasons he was making the album in the first place — every child’s desire to take back control, to be heard, to tell the story as it should be told: “I guess I just wanted to have the last word,” he said.

Shortly before the release of the album, Thompson took stock of the project, one that came out of a time when, as he put it, he was “desperate to have my family around me.” He was pleased with the mix of contributions: his sister’s pop brightness, his mother’s Celtic ballad, his nephew’s brainy guitar chops. He took particular satisfaction from the final result of one of his father’s contributions, a song called “That’s Enough,” an anthemic condemnation of failed political promises. “He didn’t address that this is a family album — he didn’t address the issue, which is just like him,” Teddy said. But Teddy was proud of the work he himself brought as a producer to the sound. “Everybody’s in the right place, and no one’s sticking out,” he said. “It was difficult to make it sound like everyone’s together, because we weren’t — which is exactly the way my family is. If anything, that kind of sums up the whole process. It’s trying to bring everybody from wherever they are, in their own little world. And make it sound like we’re a family.”