Bossa Nova. Tom Jobim. Jazz. Brazil

He had a big comeback in 1983 with the Barry Mann & Cynthia Weil power ballad “Never Gonna Let You Go,” which reached the top five on the Hot 100. He enjoyed another rediscovery in 2006 when his album Timeless, which he co-produced with will.i.am, reached No. 44 on the Billboard 200 and received a pair of Grammy nods. (The album featured such guest artists as The Black Eyed Peas, Erykah Badu, Stevie Wonder, John Legend and Justin Timberlake.) In 2012, he was nominated for an Oscar for best original song for a song he co-wrote for the film Rio.

Mendes won a Grammy for best world music album for his 1992 album Brasileiro and two Latin Grammys for best Brazilian contemporary pop album for Bom Tempo and Timeless. He received a lifetime achievement award from the Latin Recording Academy in 2005.

In 1966, Mendes came to the attention of Herb Alpert, co-founder of A&M Records, and one of the top-selling album artists of the 1960s. Alpert produced the group’s first three albums, all of which went gold. Alpert also took Brasil ’66 on tour with him and even wrote an enthusiastic recommendation that appeared on the back cover of their debut album: “One afternoon recently, a friend of mine called to ask if I wanted to hear a new group. From the first note I was grinning like a kid who’d just found a new toy.” That album remained on the Billboard 200 for more than two years (a rarity in those days) and was voted into the Grammy Hall of Fame in 2012.

Alpert was a close friend of Mendes’ for nearly 60 years. “Sergio Mendes, my brother from another country, passed away quietly and peacefully,” Alpert said in a statement on Friday. “He was a true friend and extremely gifted musician who brought Brazilian music in all its iterations to the entire world with elegance and joy.” (Another bond between the two musicians: Lani Hall, to whom Alpert has been married since 1973, was one of two female singers in Sergio Mendes & Brasil ’66.)

The group’s sound was cool, yet hot, and brimming with confidence. Still, it was a new sound in 1966, so new that A&M took no chances and supplied parenthetical phonetic spellings for five song titles on the album, including “Mais Qu Nada (Ma-sh Kay Nada).” That pronunciation gambit may seem quaint in an era when Bad Bunny gives acceptance speeches on general-audience award shows in Spanish, but, hey, baby steps. One generation paves the way for the next.

The group’s music was often featured in “lounge music” compilations of pop songs from the 1960s, which were a forerunner to today’s “yacht rock” collections of pop songs from the 1970s and 1980s. Some people, it seems, can only enjoy pop music if they’re being ironic about it. (But they’re listening, so I’ll take it.)

Here are 10 Mendes tracks which will remind you of his greatness or give you a good place to start in exploring this talented and innovative musician.

I wrote the liner notes for a CD compilation, Sergio Mendes & Brasil ’66-86, which was released in 1987 amid A&M’s 25th anniversary celebration. This piece draws some material from those notes.

Hot 100 peak: NA

From the album: Encanto

Notes: This track, featuring Brazilian singer Vanessa Da Mata, was featured on Encanto, which was the second Mendes album that he co-produced with will.i.am. Encanto topped Billboard’s Jazz Albums chart and reached No. 60 on the Billboard 200. This song, which Mendes co-wrote with Da Mata, received a Latin Grammy nod for best Brazilian song (Portuguese language).

Hot 100 peak: NA

From the album: Herb Alpert & the Tijuana Brass

Notes: The Brasil ’66 concept grew out of the worldwide popularity of Brazilian music in the early ’60s. Songs composed by Antonio Carlos Jobim, including “Desafinado” and “The Girl From Ipanema,” were major pop hits, and Bossa Nova became an international craze. This witty coupling of “One Note Samba,” composed by Jobim, and “Spanish Flea,” which Alpert had included on his megahit 1965 album Whipped Cream & Other Delights, saluted both of these men, who were so crucial in Mendes’ career. Hearing “Spanish Flea,” which became iconic through its use on the 1960s game show The Dating Game, will make boomers smile.

Hot 100 peak: NA

From the album: Equinox

Notes: This sprightly gem was drawn from the group’s second album, released in the spring of 1967. João Gilberto composed the song circa 1956. It is considered one of the first bossa nova songs. Listening to this version, it’s easy to hear Brasil ’66’s influence on Manhattan Transfer or even on Finneas as he looks for arrangement ideas for Billie Eilish.

Hot 100 peak: NA

From the album: NA

Notes: Mendes received an Oscar nomination for best original song in 2012 for this zesty song from the film Rio, which blends elements of samba, carnival and hip-hop. Mendes composed the melody withCarlinhos Brown. Siedah Garrett wrote the lyric. This was the year there were just two nominees in the category, the lowest number in Oscar history. “Real in Rio” lost to “Man or Muppet” from The Muppets, the only song from a Muppet movie ever to win an Oscar.

Hot 100 peak: No. 4

From the album: Look Around

Notes: A great song can be interpreted in any number of ways. Dusty Springfield reached No. 22 on the Hot 100 in November 1967 with a slow, sensuous version of this Burt Bacharach/Hal David classic, which she had sung on the soundtrack to the film Casino Royale, but this smartly-arranged cover version was even bigger hit. It reached No. 4 on the Hot 100 after Mendes and Brasil ’66 performed it on the Oscars in April 1968 (where it was nominated for best original song). Janis Hansen sang lead, making this one of the few key Brasil ’66 songs where Lani Hall wasn’t out front. Fergie and will.i.am were featured on the remake version that kicked off Mendes’ 2008 album, Encanto.

Hot 100 peak: NA

From the album: Look Around

Notes: Alan and Marilyn Bergman co-wrote this haunting, hypnotic ballad, which features the kind of romantic lyric they just don’t write anymore: “How I envy a cup that knows your lips.” The song was featured on the B side of a top 10 hit – “The Look of Love.” “Like a Lover,” an English-language version of “O Cantador,” has been recorded by Carmen McRae, Sarah Vaughan, Dianne Reeves, Al Jarreau and Natalie Cole, among others.

Hot 100 peak: NA

From the album: Look Around

Notes: The Bergmans also co-wrote this exquisite song, which also was on the B side of a top 10 hit – “The Fool on the Hill.” “So Many Stars” has been recorded by such great singers as Tony Bennett, Sarah Vaughan, Barbra Streisand and Natalie Cole. This showcase for Lani Hall shows that she belongs in that company.

Hot 100 peak: No. 62

From the album: Crystal Illusions

Notes: The Bergmans also co-wrote this song. The song features a bouncy arrangement and a flower-power lyric (“nothing else to make but breakfast and love”) that stamp it unmistakably as a product of the ’60s. But it also includes this timeless and endearing romantic invitation: “We’ll hang a little sign that just says, Paradise, Population: 2.” The song is a gem of simplicity and understatement.

Hot 100 peak: No. 6

From the album: Fool on the Hill

Notes: The group’s sprightly arrangement of “The Fool on the Hill” borrows liberally from Bacharach’s style and suggests what might have happened if Bacharach had produced The Beatles. The song brought Brasil ’66 a Grammy nod for best contemporary-pop performance, vocal duo or group – where it competed with The Beatles’ “Hey Jude.” (Neither won. The prize went to Simon & Garfunkel’s “Mrs. Robinson.”) Surprisingly, this was Brasil ’66’s only Grammy nod. (Mendes has landed five additional nods as a solo artist.) Mendes performed the song at the 2015 MusiCares Person of the Year tribute concert, when Paul McCartney was the honoree.

Hot 100 peak: No. 47

From the album: Sergio Mendes & Brasil 66

Notes: This song was written and originally recorded in 1963 by Portuguese composer Jorge Ben. Mendes’ version rode the Hot 100 for eight weeks in 1966, opening Americans’ ears to Latin rhythms. (The title was frequently misspelled “Mas Que Nada”). The song hit the Hot 100 the same month that future Latin music icon Gloria Estefan turned nine, which shows you how early in the game this was. A new version of the song from Timeless, featuring The Black Eyed Peas, received a Grammy nomination for best urban/alternative performance and a nod at the Latin Grammys for record of the year.