Throughout Tony Bennett's long, remarkable career, it's possible to trace the evolution and endurance of vocal pop and jazz in the 20th century. Unlike his idol Frank Sinatra, Bennett was too young to be part of the first wave of the Great American Songbook in the years before World War II. He achieved his national breakthrough in 1951, when the charts were dominated by soft-focused orchestral pop and novelties, music that Bennett himself would often sing during his early years. Occasionally, he was given the opportunity to sing jazz while recording for Columbia in the '50s, but it was a pop song that turned him into a superstar in 1962: "I Left My Heart in San Francisco," a song styled after the classic pop of the prewar era. "I Left My Heart in San Francisco" turned into an enduring standard of the 20th century but, for a while, its popularity eclipsed that of the singer who popularized the tune. Bennett didn't weather the '60s well, thanks to record companies that attempted to modernize his sound, and while he had an artistically fruitful '70s on his short-lived independent label Improv -- he recorded albums with pianist Bill Evans that established his jazz bona fides -- he suffered a series of personal problems that left him at rock bottom at the dawn of the '80s. It was then he achieved one of the greatest comebacks in pop music history. Hiring his son Danny as his manager, he reunited with his music director/pianist Ralph Sharon and began targeting younger audiences without shedding his longtime fans. This strategy paid off in the '90s, when 1992's Perfectly Frank topped Billboard's jazz charts and went gold. Bennett's crossover to the pop mainstream seemed to culminate with 1994's MTV Unplugged, an unexpected hit that took home the Grammy for Album of the Year, but it turned out his revival was no flash in the pan. Bennett stayed in the spotlight beyond the '90s, not only maintaining his audience but building it through a series of duets with stars as diverse as Lady Gaga and Diana Krall. Through it all, Bennett remained a skilled, charismatic practitioner -- and vocal advocate -- for classic American pop until his death in 2023.

The son of a grocer, Tony Bennett was born Anthony Dominick Benedetto on August 3, 1926. Raised in Astoria, Queens, by Italian emigrants -- his father, John, was a recent arrival from Reggio Calabria, and his mother, Anna, was born to natives of the Calabria region who headed to the States in 1899 -- Bennett suffered from poverty and ill fortune as a child, yet he also cultivated an interest in art and music. By the time his father died when Tony was ten, he was already singing professionally, notably performing alongside Mayor Fiorello La Guardia at the opening of the Triborough Bridge in 1936. As a teenager, Bennett had several gigs as a singing waiter, and he enrolled in New York's School of Industrial Art, studying music and painting. When times got tight in his family, he dropped out of school to support his mother and siblings, making money once again as a singing waiter.

Bennett was drafted into the Army in 1944, during the final year of World War II. Stationed in Europe, he saw combat in France and Germany; he was also part of the liberation of a Nazi concentration camp outside of Landsberg. Staying in Germany as part of the occupying force, he sang in a Special Services band before his discharge in 1946. Upon returning home, he attended the American Theatre Wing under the G.I. Bill, all the while working as a singing waiter.

During 1949, Bennett's career began to take off. While working under the stage name Joe Bari, he recorded a version of George & Ira Gershwin's "Fascinating Rhythm" for Leslie, a single that didn't go anywhere but did coincide with the singer catching the attention of Pearl Bailey. She hired him to open for her at a Greenwich Village concert, which was attended by comedian Bob Hope. Taken by the singer then known as Joe Bari, Hope invited the vocalist on tour on the provision he change his name. Deeming Anthony Bendedetto too long for a marquee, Hope shortened the singer's name to Tony Bennett.

Things began to happen quickly for Bennett after this point. In 1950, he recorded a demo of "The Boulevard of Broken Dreams," on the basis of which Mitch Miller signed him to Columbia Records. The label was steeling itself for the departure of Frank Sinatra, who feuded often with Miller. Bennett eased into his vacancy by singing chart-friendly pop tunes, starting with "Because of You," which was buttressed by an arrangement by Percy Faith. It reached number one in September 1951, followed quickly by a cover of Hank Williams' "Cold, Cold Heart." This single also reached number one, its success often cited as elevating Hank Williams' reputation outside of the South and country music circles. "Cold Cold Heart" also proved Bennett wasn't a one-hit wonder, either. During 1952, he racked up three hit singles, the biggest of which was "Here in My Heart," which peaked at 15, and he reached the top of the charts again in 1953 with "Rags to Riches," which was followed quickly by the number two single "Stranger in Paradise," a song taken from the Broadway musical Kismet. Bennett charted regularly over the next two years, with a handful of songs breaking into the Top 10 -- "There'll Be No Teardrops Tonight" and "Cinnamon Sinner," both from 1954 -- before the pop charts were changed irrevocably in 1956 by the rise of rock & roll.

While Bennett didn't disappear from the single charts in the second half of the '50s -- "Can You Find It in Your Heart?" went to 16 in 1956, the same year that "From the Candy Store on the Corner to the Chapel on the Hill" peaked at 11; he cracked the Top Ten in 1957 with "In the Middle of the Island" -- but shifted his attention to adult-oriented formats, such as albums and nightclubs, which allowed him to indulge in his love of jazz. On 1957's The Beat of My Heart, he collaborated with arranger Ralph Sharon -- a pianist who would become Bennett's accompanist and musical director -- on an album that featured saxophonist Nat Adderley and emphasized percussionists Chico Hamilton, Art Blakey, Sabu, and Jo Jones. In 1959, he released In Person!, a live album where he was backed by the Count Basie Orchestra; Bennett returned the favor by recording Strike Up the Band with Basie's Orchestra. As the '50s gave way to the '60s, Bennett increasingly specialized in swinging and soft versions of the Great American Songbook, mining territory pioneered by Frank Sinatra.

Sharon brought "I Left My Heart in San Francisco," a song written by recent New York city transplants George Cory and Douglass Cross, to Bennett in late 1961. Tennessee Ernie Ford previously passed on the song but Bennett recorded it in early 1962, with Columbia placing it on the B-side of "Once Upon a Time." DJs preferred "I Left My Heart in San Francisco" to its flip and the ballad started its steady climb up the charts, peaking at number 19 but staying on the charts for the lion's share of 1962. An album named after the hit was rushed onto the market, reaching number five on Billboard's Top 200, and the song garnered Grammy awards for Record of the Year and Best Solo Vocal Performance, Male. The success of "I Left My Heart in San Francisco" wasn't limited to 1962: it turned into an enduring standard, earning an induction into the Grammy Hall of Fame and selected for preservation in the National Recording Registry by the Library of Congress.

"I Left My Heart in San Francisco" may have turned Bennett into a superstar but he didn't remain at the top of the charts for much longer. Immediately after its success, he had Top 20 hits in 1963 with "I Wanna Be Around" and "The Good Life," but the following year saw the British Invasion sweeping America, dramatically decreasing the space for adult-oriented pop in the Top 40. Bennett continued to record easy listening material through the '60s, sometimes scraping the bottom of the Top 40, usually placing high on Billboard's Easy Listening charts between 1964 and 1966. "Who Can I Turn To (When Nobody Needs Me)" reached three on Easy Listening in 1964, with "If I Ruled the World" and "The Shadow of the Smile" making it to eight on the same chart the following year, and "A Time for Love" reached three in 1966.

In 1967, Bennett dipped his toe into contemporary pop with a cover of Stevie Wonder's "For Once in My Life." This shift was instigated by the new president of Columbia, Clive Davis, who was intent on modernizing his easy listening singers. Bennett reluctantly agreed to pursue this path, releasing covers of Jimmy Webb's "MacArthur Park" and George Harrison's "Something" in 1969 and 1970. Both singles were modest easy listening hits and were featured on the 1970 LP Tony Sings the Great Hits of Today!, an album Bennett would later claim made him physically ill to record. Neither the album nor its swift sequel Tony Bennett's Something (which once again featured the Beatles song on record) revitalized the singer's commercial fortunes, so Columbia rode out his contract over the next year, parting ways with Bennett after 1972's With Love.

Bennett's departure from Columbia kick-started a turbulent decade for the singer, one where he bounced between labels as he struggled with a variety of personal problems. Verve signed him in 1972, releasing The Good Things in Life that fall, but the association was short-lived: one more album, Listen Easy, followed in 1973 before they parted ways. During his brief stint with the label, Bennett also hosted a British television show called Tony Bennett at the Talk of the Town. He next moved to Los Angeles, where he founded his own label, Improv, with the assistance of Bill Hassett in 1975. Improv was hobbled with distribution problems that would lead to its early dissolution in 1977, but the five albums Bennett recorded for the imprint were instrumental in raising his reputation as a jazz singer, particularly the pair of albums he cut with pianist Bill Evans: 1975's The Tony Bennett/Bill Evans Album -- which reached 31 on Billboard's Jazz albums chart -- and its 1976 sequel Together Again. Left without a label, Bennett wound up performing regularly in Las Vegas, suffering through drug addiction, financial problems, and the dissolution of his second marriage.

Bennett turned his career around by hiring his son Danny as his manager. Danny Bennett moved his father back to New York City and off the Vegas circuit, lining up a series of shows in intimate venues instead. The singer also reunited with pianist Ralph Sharon, who'd served as his musical director in the early '60s. Bennett worked steadily as a live performer but made his comeback as a recording artist in 1986 when he released The Art of Excellence, his first album for Columbia in 14 years. The Art of Excellence began a renaissance period for Tony Bennett, one that proved to last for decades. While his son cannily booked his father on television shows appealing to younger demographics, Bennett maintained his allegiance to pre-war vocal pop and jazz, becoming the torch bearer for the Great American Songbook.

Astoria: Portrait of the Artist, a 1990 album where Bennett gazed back at his past, consolidated the artistic gains of The Art of Excellence, and the 1991 box set Forty Years: The Artistry of Tony Bennett made a case for his enduring legacy but it was his 1992 Sinatra tribute Perfectly Frank that was the catalyst for his remarkable crossover success in the '90s. Perfectly Frank topped the Billboard Jazz chart -- it made it to 102 on the Top 200, his best placement since 1971 -- on its way to winning the Grammy for Best Traditional Pop Vocal Performance, a category Bennett would dominate over the next decade; it also became his first album to be certified Gold since 1967's Tony's Greatest Hits, Vol. 3. Steppin' Out, its 1993 sequel, saluted Fred Astaire, and along with replicating its predecessor's success -- it took home the Best Traditional Pop Vocal Performance Grammy, topped the Jazz albums chart, and went Gold -- it also received some play on MTV for its title track. This opened the door for Bennett's appearance on MTV Unplugged in 1994, a performance that was released as an album in April 1994. Featuring guest appearances by k.d. lang and Elvis Costello, MTV Unplugged turned into smash hit, reaching 48 on Billboard's Top 200 (it also topped their Jazz chart), achieving Platinum certification and winning the Grammy not just for Best Traditional Pop Vocal, but Album of the Year.

After MTV Unplugged, Bennett rode a hot streak that lasted well into the 21st century. He remained a popular concert attraction and recorded regularly, often alternating thematic tribute records with duet albums. Here's to the Ladies, the 1995 set which was his first studio album since Steppin' Out, found him singing songs usually associated with female vocalists, while 1997's On Holiday was a salute to Billie Holiday; both took home Grammys for Best Traditional Pop Vocal Performance, as did 1999's Bennett Sings Ellington: Hot & Cool. Peaking at 50 on the Top 200 and going Gold, Playin' with My Friends: Bennett Sings the Blues, a 2001 collection, was his biggest hit since MTV Unplugged, but it was eclipsed by 2002's duet album with k.d. lang, A Wonderful World, which reached 41 and went Gold; both records won the Grammy for Best Traditional Pop Vocal Album, as did 2004's The Art of Romance.

Bennett celebrated his 80th birthday in 2006 with the release of Duets: An American Classic. Featuring guest appearances by a host of pop stars including Elton John, Paul McCartney, and George Michael, the album rivaled MTV Unplugged in popularity, peaking at three on the Billboard Top 200 and earning a Platinum certification. Its 2011 sequel, Duets II, bested its predecessor by entering the charts at number one; both albums took home the Grammy for Best Traditional Pop Vocal Album. Viva Duets, a collection of duets with Latino singers, peaked at five in 2012.

Tony Bennett's next big hit was Cheek to Cheek, a collection of jazz standards recorded with Lady Gaga. Released in September 2014, Cheek to Cheek debuted at number one on the Billboard Top 200 and wound up winning the Best Traditional Pop Vocal Album Grammy. In 2015, Bennett teamed up with pianist Bill Charlap for The Silver Lining: The Songs of Jerome Kern, a jazz-oriented effort that was another Traditional Pop Vocal Album Grammy winner. Bennett marked his 90th birthday in 2016 with an all-star concert held at Radio City Music Hall. Featuring k.d. lang, Lady Gaga, Michael Bublé, and Andrea Bocelli, the concert was released as the live album Tony Bennett Celebrates 90. In September of 2018, Bennett released Love Is Here to Stay, a duet album with Diana Krall that doubled as a tribute to George Gershwin.

Early in 2021, Bennett revealed to AARP Magazine that he was diagnosed with Alzheimer's disease in 2016. His doctors believed his active schedule of performing and recording kept his brain stimulated during the initial years after his diagnosis, but once he was forced off the road due to the COVID-19 pandemic in 2020, he and his son Danny decided the time was right for the singer to retire. Early in August 2021, Bennett gave a pair of Radio City Music Hall concerts, after which his team announced they'd be his last shows. In October, Bennett released Love for Sale, his second duet album with Lady Gaga. The pair had recorded the album between 2018 and 2020, focusing on Cole Porter songs. The album proved to be Bennett's swan song. His remarkable life and career came to an end with his death in New York City on July 21, 2023, at the age of 96. ~ Stephen Thomas Erlewine

A glamorously gaudy, self-made, post-modern diva stitched together from elements of Madonna, David Bowie, and Freddie Mercury, Lady Gaga was the first millennial superstar. Mastering the constant connection of the Internet era, Gaga generated countless mini-sensations with her style, her videos, and her music, cultivating a devoted audience she dubbed "Little Monsters." But it wasn't just a cult that turned her 2008 manifesto The Fame into a self-fulfilling prophecy: Gaga crossed over into the mainstream, ushering out one pop epoch and kick-starting a new one, quickly making such turn-of-the-century stars as Christina Aguilera and Britney Spears seem old-fashioned. It was quite a trick for any artist to pull off, but especially impressive for one who specialized in repurposing the past (particularly the '80s) for present use, creating sustainable pop for a digital world. Gaga's fame soon extended beyond music: she received accolades for her 2015 role in American Horror Story: Hotel and her Oscar-nominated turn in Bradley Cooper's 2018 remake of A Star Is Born. Within two years, she returned to the top of the Billboard 200 with Chromatica, then notched another Top Ten with her second standards album, Love for Sale.

Perhaps unsurprisingly given her flair for grand gestures, Lady Gaga has deep roots in drama. Born Stefani Germanotta on March 28, 1986, the future Gaga played piano as a child and pursued musical theater in high school, regularly auditioning for New York-based television shows, notably landing a background role for a 2001 episode of The Sopranos. At the age of 17 she enrolled at New York University's Tisch School of the Arts in their Collaborative Arts Project 21. As she studied, she continued to eke her way into show biz, winding up with an appearance on MTV's short-lived post-Punk'd reality show Boiling Points in 2005. Not long afterward, she left school so she could concentrate on her music, fronting a band called SGBand, which released two EPs prior to splitting. Germanotta then teamed with producer Rob Fusari, a collaboration that produced not only her stage name Lady Gaga, but recordings that led to her signing with Def Jam in the fall of 2006.

Her association with Def Jam was short-lived: the label dropped her early in 2007. Gaga rebounded by working with performance artist Lady Starlight, the two developing the Lady Gaga & the Starlight Revue, a tongue-in-cheek neo-burlesque act that gained positive press and proved to be her last stop before signing with Interscope later in 2007. While at Interscope, she created a bond with Akon, who convinced Interscope head Jimmy Iovine to have her co-sign with his Kon Live imprint, and Gaga began working with producer/songwriter RedOne, a union that led to the songs that would bring her fame: "Just Dance," "LoveGame," and "Poker Face." These songs formed the foundation of The Fame, the debut album that appeared in August 2008.

Initially, Lady Gaga had greater success in Europe, thanks in large part to the "Just Dance" single, which earned club play in the U.S. and chart placement in other territories. Gaga's march toward the top of the American chart was slow but "Just Dance" reached the peak position in January 2009, followed swiftly by "Poker Face," the single that firmly pushed her into the mainstream, its popularity growing so large it often functioned as a punch line on TV in addition to winning a Grammy for Best Dance Recording. "LoveGame" and "Paparazzi" also appeared as singles before Gaga released The Fame Monster in time for the holiday season of 2009. The mini-LP, available separately and as a package with The Fame, contained the single "Bad Romance," whose popularity soon rivaled "Poker Face" and helped kick-start a stellar year for Gaga in 2010. That year, the hit singles "Bad Romance," "Alejandro," and the Beyoncé duet "Telephone," along with the successful Monster Ball Tour, put Lady Gaga front and center with the public as she worked on her sophomore album, announcing its May release on New Year's Day 2011.

The steady march to the summer unveiling of Born This Way was preceded by the release of three singles: "Born This Way," "Judas," and "The Edge of Glory." All of them reached the Top Ten, and the empowerment anthem "Born This Way" hit number one soon after its release in February 2011. The accompanying album arrived to mixed reviews, but it eventually reached double-platinum status and produced subsequent hits with the Top Ten "You and I" as well as a Top 40 entry for "Marry the Night." A full remix of the album, naturally called Born This Way: The Remix, appeared at the end of the year, as did a holiday television special called A Very Gaga Thanksgiving and an accompanying EP, A Very Gaga Holiday.

Gaga continued to promote Born This Way throughout 2012, appearing at various star-studded events and on television programs while continuing her international tour. The tour came to a halt in February of 2013, when she announced that she needed hip surgery to repair a labral tear. As she was healing, she worked on her third album, Artpop. Preceded by the Top Ten single "Applause" and the Top 15 follow-up "Do What U Want" (the latter a duet with R. Kelly), Artpop was released in early November 2013. The album explored familiar themes of fame, love, and empowerment. It debuted at number one in several countries, including the U.S.

The release of Artpop coincided with an announcement that Gaga had parted company with Troy Carter, her manager of five years. Then, shortly after she embarked on the ArtRave tour in May 2014, it was revealed that Bobby Campbell -- her new manager -- had signed them both up to Artist Nation, the artist management division of Live Nation Entertainment. That same year, Gaga worked in collaboration with fellow New Yorker Tony Bennett on an album of jazz standards titled Cheek to Cheek, which was issued in September. Cheek to Cheek provided a jolt to Gaga's career. The album debuted at number one on Billboard's Top 200 and earned the Grammy Award for Best Traditional Pop Album, its success opening the door to other snazzy show biz gigs. First, she sang a tribute to The Sound of Music at the 2015 Academy Awards and, a year later, she was nominated for a Best Original Song Oscar for "Until It Happens to You," the tune she co-wrote with Diane Warren for the documentary The Hunting Ground. Gaga was also cast as a lead in the 2015-2016 season of American Horror Story, winning a Golden Globe for her portrayal of Elizabeth.

She returned with new music on 2016's Joanne, which was inspired by her late aunt of the same name. Drawing on glam rock, disco, and folk, as well as dance-pop, the album featured an impressive list of collaborators, including Mark Ronson, Nile Rodgers, Father John Misty, Josh Homme, Florence Welsh, Tame Impala's Kevin Parker, and Beck. Featuring the singles "Perfect Illusion," "John Wayne," and "Million Reasons," the album debuted at the top of the Billboard 200 but quickly lost traction on the charts. It wasn't until February of 2017 that the success of her Super Bowl halftime show would set Joanne on the comeback trajectory. In addition to returning The Fame, Born This Way, and Artpop to the charts, the momentum from her performance landed Joanne at number two and "Million Reasons" at number four on the Hot 100. Before embarking on the Joanne World Tour, she issued the standalone single "The Cure" and the documentary Gaga: Five Foot Two, which partially focused on chronic physical ailments that would eventually cause the cancellation of the final stops of the world tour.

In 2018, Gaga made the leap to the silver screen by starring alongside Bradley Cooper in his remake of the classic Hollywood fable A Star Is Born. Upon its release in October, the soundtrack to the film debuted at the top of the Billboard and U.K. charts, while the film itself turned into a commercial and critical hit. Lady Gaga earned two Academy Award nominations for A Star Is Born: a nod for Best Actress and as a co-composer of "Shallow," which was nominated for, and won, Best Original Song. After its win, the song reached number one on the Billboard charts. In 2020, she won the Best Song Written for Visual Media Grammy Award for the A Star Is Born track "I'll Never Love Again," which she co-wrote with Natalie Hemby, Hillary Lindsey, and Aaron Raitiere.

Gaga's Grammy win arrived as she ramped up the release cycle for Chromatica, her sixth LP. A return to glitzy dance-pop, Chromatica arrived in May 2020, preceded by the singles "Stupid Love" and "Rain on Me," the latter a duet with Ariana Grande that debuted at number one on the Hot 100. Also featuring appearances by BlackPink and Elton John, the album continued Gaga's streak of number one entries on the Billboard 200. A remix album, Dawn of Chromatica, arrived in 2021 and featured contributions by Arca, Rina Sawayama, Charli XCX, and many more. That same year, Gaga remained in the spotlight, singing the national anthem at Joe Biden's inauguration ceremony, joining the cast of Ridley Scott's House of Gucci, and celebrating the tenth anniversary of Born This Way with an EP dubbed Born This Way Reimagined, which showcased covers by Kylie Minogue, Big Freedia, Orville Peck, Years & Years, and others. She also reunited with Tony Bennett for a follow-up to their 2014 collaboration, a Cole Porter tribute dubbed Love for Sale. The following May, Gaga contributed a classic arena power balled called "Hold My Hand" to the Top Gun sequel, Top Gun: Maverick. ~ Stephen Thomas Erlewine