Rufus Wainwright remembers June 14, 2006, as the night he climbed a musical Mount Everest. Or jumped off one.

“I’d never done it from top to bottom until the first night I performed it,” the singer-songwriter recalled of “Rufus Does Judy at Carnegie Hall,” his song-by-song re-creation of a legendary concert that Judy Garland performed at the same space in 1961.

Backed by a 36-piece orchestra, Mr. Wainwright summoned Garland’s restless spirit in jazzy anthems like “That’s Entertainment” and openhearted ballads like “Stormy Weather.” He even repeated some of Garland’s original banter (“Sing it with me, please!”), like a Talmudic scholar reciting a sacred text.

The result was part showbiz stunt, part postmodern happening, part fanboy dream come true. It was a 32-year-old pop star claiming Judy worship for a new, post-Stonewall generation of gay men. And it has lived on in its live-album incarnation, for which Mr. Wainwright received his sole Grammy nomination.

Now, 10 years later, he is resurrecting the concert at Carnegie Hall: a homage to a homage. After playing New York on June 16 and 17, he will take the show the following week to the Luminato Festival in Toronto, where his husband, Jörn Weisbrodt, is the outgoing artistic director.

But Mr. Wainwright is not the same performer, or person, that he was a decade ago. He is now 42, four years older than Garland was when she mounted the original concert. Still louche and languid, he has acquired a touch of silver on his sideburns and a glut of life experiences, both joyful and bruising.

Since the 2006 concert, he married Mr. Weisbrodt, fathered a child (with his longtime friend Lorca Cohen, the daughter of the singer Leonard Cohen) and weathered the ups and downs of the music business. Most life-altering was the loss of his mother, the folk singer Kate McGarrigle, who died of cancer in 2010.

All those milestones will inevitably color the Carnegie Hall repertoire, which for Garland encapsulated the glamour and mess of a life lived in emotional extremis. (She died eight years after the 1961 concert from a barbiturate overdose.)

Mr. Wainwright is no stranger to turmoil himself. The product of an eccentric musical clan (his father is the troubadour Loudon Wainwright III, and his mother was half of a Canadian folk duo with her sister Anna McGarrigle), he released his self-titled debut album in 1998, when he was 24.

He once memorably described his 20s as “gay hell”: a haze of alcohol and drug abuse, anonymous sex and emotional nihilism, which he touted obliquely in songs like “Cigarettes and Chocolate Milk,” his ode to decadence.

His debauchery went hand in hand with an obsession with Garland. “I kept having these blackouts where I would go to record stores looking to buy the latest Radiohead album and walk out with yet another ‘Greatest Hits of Judy Garland,’” he said on a recent Thursday at the Whitney Museum’s eighth-floor cafe. Part of the reason he staged the Carnegie Hall show in 2006 was “to exorcise her.”

For the most part, it worked. After New York, he took the concert to the London Palladium. But by the time he got to Paris, he had lost his voice, and the show was “a complete disaster.” He limped to the Hollywood Bowl but had “this real sinking feeling that I couldn’t continue.”

Then life got even more complicated.

Mr. Wainwright and his mother, he said, were “one of the most classic gay-son-mother duos ever,” speaking every other day. Even Mr. Weisbrodt, who had become Mr. Wainwright’s first serious romantic partner, acknowledged: “I never challenged her position. To me, it was always clear she was No. 1 and I was No. 2. But I would sleep with him.”

As her health declined, Mr. Wainwright panicked, even as he was considering becoming a parent himself. He and Ms. Cohen, whom he knew from growing up in Montreal, had discussed conceiving a child together, but mostly it was “a lovely little daydream,” he said. Then Ms. Cohen brought it up again, for real.

His mother also urged him to pursue fatherhood, perhaps sensing that he would need an emotional anchor when she was gone. That Ms. Cohen came from another Canadian musical dynasty may have given the idea some extra appeal, like a medieval alliance.

“My mother was a very ambitious woman, but mostly for her children,” Mr. Wainwright said, still palpably affected by his mother’s death but cleareyed about her flaws. “She wasn’t really able to be that way for herself, and in fact was always somewhat haunted by not being blessed with that cutthroat instinct that a lot of her colleagues had, whether it’s Bonnie Raitt or Linda Ronstadt. They were better at maneuvering the system than she was.”

Sadly his mother didn’t live to see the plan come to fruition. She died on Jan. 18, 2010, nearly a year before her granddaughter, Viva Wainwright Cohen, was born.

Suspended between grief and renewal, Mr. Wainwright sought to solidify his newfangled family. A few months after his mother’s death, he proposed to Mr. Weisbrodt over Indian food in London. (He announced the engagement the next night, onstage at the Royal Opera House.)

The couple had met in Germany, when Mr. Weisbrodt was working at the Berlin State Opera and approached Mr. Wainwright about a commission. “Rufus was very nervous about having a committed relationship,” Mr. Weisbrodt recalled. “The longest relationship he had been in was I think four weeks.”

They married in August 2012, in Montauk, N.Y., with the cabaret chanteuse Justin Vivian Bond officiating and little Viva as reluctant flower girl. Mr. Wainwright is Viva’s legal parent, but he only sees her every few months; she lives in Los Angeles with her mother, while Mr. Wainwright and Mr. Weisbrodt split their time between New York and Toronto, though they are thinking of moving out west. (He is reticent about the complicated parenting dynamic with Ms. Cohen but said, “We’re getting better all the time.”)

A death, a birth and a marriage, all in the span of two and a half years: It did a number on Mr. Wainwright. “Having my mother’s death and my daughter’s birth coincide, it was very traumatic for everybody,” he said with a rueful, nasal laugh, the kind he tends to affix to moments of gravitas.

His melancholy, along with his waggish humor, goes more unguarded in his songs. Musically, he resists categorization. His last album, “Take All My Loves,” was an adaptation of nine Shakespeare sonnets, with vocal cameos by singers like Florence Welch and William Shatner.

He has spent the last few years immersed in opera, which he calls his “favorite art form.” His first opera, “Prima Donna,” was commissioned by the Metropolitan Opera and Lincoln Center Theater, but he and the Met parted ways before it was staged. The official line was that Mr. Wainwright, who wrote the libretto in French, refused to bend to the Met’s insistence that it be in English.

Though “Prima Donna” eventually opened at the Manchester International Festival in 2009 (Mr. Wainwright came dressed as Verdi), the opera establishment never fully embraced him. In 2012, Zachary Woolfe of The New York Times described its American debut as “a tasteful, well-intentioned, ultimately mystifying failure.” (He is now working on a second opera, about the Roman emperor Hadrian.)

His forays into classical music sidetracked him from pursuing the pop megastardom he once envisioned. Though he admits to enjoying the “slings and arrows and diva hissy fits and conductors smashing batons” of the opera world, he acknowledges that it has “distanced me from the pop world.”

“And I’ve paid a price for that,” he added.

In a de facto rehearsal run for Carnegie Hall, Mr. Wainwright arrived in Annapolis, Md., last month as part of a three-night mini-tour that took him to the Rams Head on Stage, a smallish concert space adjoining a tavern.

Wearing a foppish striped blazer adorned with a twinkling brooch, he played a few of his own brooding, folky ballads, before telling the audience: “We’re going to do a few Judy songs for you. I’m not sure if you were expecting that, but that’s what you got.”

The mostly white-haired crowd seemed unfazed as he jumped to the swinging tempo of the 1938 standard “You Go to My Head.” A few verses in, he appeared to flub the words, singing “Da da beeda foona heena fa fa.” But devotees knew that this was entirely planned: It was the exact spot where Garland had forgotten the lyrics in 1961 and frantically subbed in nonsense syllables.

“Let’s get sad,” he announced after the song ended, switching to another Garland standard, the smoldering torch song “Alone Together.”

At Carnegie Hall 10 years ago, he dedicated the number to Mr. Weisbrodt. “I don’t think he would dedicate ‘Alone Together’ to me anymore,” his husband says now. “It sort of stands for someone who’s accepted that he’s in a relationship, but at the end of the day you’re always still alone.”

That isn’t the only Garland song that has shifted resonance over the decade. When Mr. Wainwright sang “The Man That Got Away” in 2006, he thought of it less as an ode to romantic abandonment (as when Garland sang it) than as a gay man’s cry of longing for a father. “My dad and I are in a much better place than we were 10 years ago,” he said of his fraught, at times openly competitive relationship with his father. “But nonetheless, when I was singing that at that time, we were struggling.”

Now, Mr. Wainwright says, “The Man That Got Away” is more about mortality, whether his father’s (who is 69) or that of his musical father figures like David Bowie and Lou Reed.

Then again, mortality seems to pervade the entire repertoire. “Death has sort of entered the fold a little bit,” Mr. Wainwright said. The generation that grew up with the original Garland album has “thinned out a bit,” meaning that the crowd that shows up this time will be even further removed from the source material.

And, of course, the loss of his mother haunts the set list, particularly Garland’s signature number, “Over the Rainbow.” When Mr. Wainwright sang it in 2006, he brought his mother out to accompany him on the piano, joking about how she would volunteer him to sing it as a child “to sober up adults at 3 in the morning.”

This time around, Mr. Wainwright plans to start singing the song a cappella, letting his mother’s absence linger before the orchestra floods in.

“That’s still her song, and now she is over the rainbow,” he said, before letting out another mournful laugh.