Tony Bennett

with Antonia Bennett Wednesday, Feb. 11, 7:30 p.m.
$66–$125 DPAC
123 Vivian St., Durham

Tony Bennett has sashayed around the music business’s block long enough to know that the kids matter. On Sunday night, when the Grammys offer pop music its biggest chunk of prime-time exposure not surrounded by a football game, the 88-year-old Queens-born crooner will wink to the youth yet again.

Each year, the Grammys strive to navigate the uneasy, unpredictable boundary between kowtowing to music-industry muscle and producing a show worthy of younger pop fans’ interestssomething they’ll like, something they’ll remember. This year, the National Academy of Recording Arts and Sciences will resort to a familiar trick, a torch-passing docket that pairs legends with up-and-coming stars. The louche Welshman Tom Jones will croon with the screechy Brit Jessie J. The chameleonic songbird Annie Lennox joins the ultra-emotive Hozier. Bennett, a Grammy perennial, will team with the divisive and artistic Lady Gaga.

This is neither Bennett’s first attempt to court the kids nor his first encounter with Gaga. In the early ’90s, his son, Danny, aggressively sent his father in search of the youth market by booking him on late-night television’s more sardonic offerings and alongside the Red Hot Chili Peppers at 1993’s MTV Video Music Awards. In 1994, he took to the cozy confines of MTV Unplugged to run through standards like “I Left My Heart In San Francisco.” The resulting record wound up nabbing the Album of the Year trophy at the 1995 Grammys, besting Seal and Clapton, Bonnie Raitt and The Three Tenors. And as though on 20th-anniversary cue, Bennett returned to the youth-culture well last fall with Cheek To Cheek, an album of standards cut with Gaga. But it might not have been the reputation resuscitation he’d hoped.

Pairing pop stars across eras is one de rigueur practice of the music business that makes logical sense. The Red Hot Chili Peppers’ appearance during the 2014 Super Bowl halftime show might have been a hot mess, but rock fans who tuned in to see Flea bounce around might have been impressed by the musicianship of Bruno Mars. This month, Jimmy Kimmel Live! will engage in era-spanning that outstrips the Grammys in artists and puns alike. Wee-Z Top will bring together Weezer’s nerdy charm and ZZ Top’s Texas cool, while Morris Day and the Haim will pair the spitfire frontman of The Time with the jittery pop of the three Los Angeles sisters.

These partnerships go best when the benefits work both ways, giving younger fans perspective on where their favorites came from and offering older listeners assurance that the kids just may be all right.

But in the case of Gaga and Bennett, the question of just whose reputation was getting burnished was tough. It seemed obvious to assume that the 28-year-old singer would essentially offer Bennett’s career a facelift by giving him a new, nubile audience. But Gaga was the one who’d just suffered a severe career misfire, thanks to her 2013 album, Artpop.

During Artpop‘s genesis in 2012, Gaga often referred to it as “experimental,” saying in one fan chat it was “a bit more modern … you never know if radio is ready.” A hip injury that required surgery forced her to cancel a slew of dates on 2013’s Born This Way Ball Tour.

Five months after that tour’s last scrapped date, “Applause,” the new album’s first single, finally landed. It was clear that she had faulted: Though the chorus was catchy enough, it felt more unfinished than avant-garde. It peaked at No. 4 on Billboard‘s Hot 100, a striking low for a lead cut by someone with Gaga’s star power.

The suffering compounded. The record’s second single, “Do What U Want,” was its strongest effort, a syrupy, eros-packed dance track that seemed destined for the tops of charts. But it was born at a bad time. Gaga’s duet partner for the tune was R. Kelly; just as the song’s promotional wheel started to spin, new details about his sexual exploits with underage women emerged, prompted in part by The Village Voice. It peaked at No. 13 on the Hot 100 and got a hasty Christina Aguilera-assisted rework. Except for an excerpt leaked by TMZ, the song’s perverse Terry Richardson-directed video was never released. It’s hard not to see Cheek To Cheek, which arrived as Gaga finished her 2014 ArtRave Ball tour, as a bit of Artpop triage.

Gaga epitomizes the ways in which the music industry struggles to negotiate just what makes a pop star these days. Her older songsthe pouty “Paparazzi,” the boisterous “Born This Way,” the ahead-of-its-time “Poker Face”maintain a strong presence on radio formats safe enough to be played in grocery stores and taxis. But on Artpop, Gaga got a little too weird for those situations, thanks to clunky jokes about Uranus and production that sounded forgotten.

Amid that album’s strange trappings, Cheek to Cheek sought to offer a reminder that she could, you know, sing. Her ability to belt out lighter-worthy ballads like “Yoü And I” or to navigate nimbly through standards like “Anything Goes” didn’t suffer from Artpop‘s structure-less offerings. Working with Bennett on Cheek To Cheek allowed her to put that voice back in its proper place, though, to prove she’s not just a Jeff Koons- or Marina Abramović-worshiping flake.

Perhaps Kanye West is looking for similar redemption: Filled with bile and self-loathing, his 2013 album, Yeezus, was dissonant and difficult, at least until its final track, the Charlie Wilson-assisted love song “Bound 2.” With the support of the 60-year-old soul singer, the song represented a redemptive ride toward the sunset for the character West played. Its video, which co-starred West’s real-life love Kim Kardashian, made that ideal explicit.

West kept quiet musically until New Year’s Eve, when he released “Only One,” a delicate, Autotune-heavy track that he claims was spiritually assisted by his late mother, Donda. Also assisting West on the track? Another elder, Paul McCartney.

West has not been shy to boast that he’s perched on art’s vanguard. Such declarations help turn him (and, similarly, Gaga) into prickly personalities, anathema to the humility-demanding American public. Macca, though, might be as high on the “culturally beloved musicians” list as West is low. By working with McCartney on his forthcoming album, West forces those who might think less of hip-hop than of the Beatlesor, hell, might simply dislike his proclivity toward fur coatsto take him seriously.

By choosing to release splashy products backed by towering figures from the old days, Gaga and West engage in a clever bit of boundary-pushing: They move forward in the public consciousness by not just acknowledging the past but asking a humble, huge favor of it.