In Party Like It’s 1999, I’m marking my birthday June 25th by reviewing every Billboard Hot 100 #1 hit from my birth year 1999 along with other notable hits from the year.

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Santana- “Smooth” (feat. Rob Thomas)

HIT #1: October 23, 1999

STAYED AT #1: 12 weeks (including 11 weeks in 1999)

Think about all those big rock bands of the ‘90s. Pearl Jam, Radiohead, Red Hot Chili Peppers, Foo Fighters. Now imagine any of them making a comeback today and enjoying the biggest hits of their career mainly by collaborating with younger artists. Imagine these acts absolutely dominating the charts like they never did before. (Something along those lines happened last year with Billy Ray Cyrus’ appearance on Lil Nas X’s chart-dominating behemoth “Old Town Road.” We’ll get to that eventually.) 

That’s what happened with Santana. The group, led by guitarist Carlos Santana, originally made their name in the psychedelic club scene of San Francisco in the late ‘60s before breaking out with their legendary acid-fueled performance at Woodstock. Soon, they were a guaranteed hit machine at the turn of the ‘70s releasing three hit albums as well as a few major hit singles. But with band changes and shifting musical styles they fell off the mainstream. It looked as if Santana was forever going to be a relic of the Woodstock era. 

That is until 1999’s Supernatural, a carefully calculated mainstream project that brought Santana back in a big way becoming the best-selling album of the band’s career selling over 30 million copies worldwide. The album was one of the best-selling albums of both 1999 and 2000 in the United States launching with “Smooth,” an immortal summer jam that became the band’s first #1 hit 30 years after their initial chart debut, a chart record that they still hold today. We’ve seen comebacks in pop music but I don’t think there’s anything that has ever come close to Santana’s comeback.

I’ve mentioned before about how despite 1999 being remembered as a teen-centric year when it comes to music the baby boomers weren’t quite ready to give up their reign over the charts as shown by Cher’s “Believe,” Billboard’s biggest single of 1999. But it at least made sense with Cher, an icon who had enjoyed varying levels of success over three decades up to that point. People still knew about Cher. It made less sense with Santana who hadn’t made much public impact since their early ‘70s peak and were inducted into the Rock and Roll Hall of Fame in 1998. Their legacy was already secure but the massive success of “Smooth” surely didn’t hurt.

Born in the Mexican city of Autlán, Carlos Santana had settled in San Francisco by 1966 when he formed the Santana Blues Band with fellow guitarist Tom Fraser. As the band’s lineup fell into place, the name was shortened to just Santana where they became an instant favorite in the San Francisco club scene thanks to their unique blend of Latin rhythms with the blues and psychedelic rock that were popular at the time along with Carlos Santana’s undeniable guitar-playing talent. It was enough to get the attention of legendary music promoter Bill Graham who became Santana’s manager booking them shows at his Fillmore West club and getting the group a major label deal with Columbia Records. 

During this time, Graham was asked to help organize the Woodstock festival and only agreed to do it if his acts were going to perform which included Santana. Despite the band having little profile not even having an album out yet, Graham got his wish. Santana performed a 45 minute set in the afternoon of the festival’s second day that mostly included songs from their upcoming debut album. The band went into Woodstock as the lowest paid and most unknown of the acts performing but came out as arguably the most talked-about performance becoming the ‘60s version of a viral sensation. When people talk about Woodstock and the best moments, Santana’s performance is usually at the top of the list. 

Santana’s self-titled debut album was released two weeks after Woodstock and thanks to the exposure and acclaim of the performance the album was a hit. On Billboard, the album peaked at #4 but stayed on the charts for over two years. Billboard named Santana as the #5 best-selling album of 1970 between the Beatles’ Abbey Road and Rare Earth’s Get Ready. Their sophomore effort 1970’s Abraxas did better going all the way to #1 as well as their next album 1971’s Santana III which featured future Journey guitarist Neil Schon. Billboard named Abraxas as the #5 best-selling album of 1971 between Janis Joplin’s Pearl and the Partridge Family’s The Partridge Family Album. Right away, Santana were a big deal helping to popularize what we now know as Latin rock.

Their success wasn’t limited to the albums. Santana yielded “Evil Ways,” a classic rock half-sung half-instrumental jam that peaked at #9 in 1970. (It’s a 9.) Abraxas yielded their superior cover of Fleetwood Mac’s “Black Magic Woman” and it performed better peaking at #4, their highest-charting single before “Smooth.” (It’s another 9.) Those were their Top 10 hits but their early success also included “Oye Como Va” a legendary cover of the Tito Puente cha-cha standard and “Everybody’s Everything” which peaked at #13 and #12 respectively. The success wouldn’t last for long.

Soon after Santana III, much of the original band members left as Carlos began to take more artistic control turning the band from a collective performing unit to the Carlos Santana Show. For the next few years, Santana made a few albums that ventured into jazz fusion abandoning their Latin rock roots. Those albums performed well at first but the shift in musical direction alienated their audience leading to declining sales for the rest of the ‘70s. For the next decade, the band ventured all over the place musically trying to see what would stick in bringing them back to their early success all while band members came and went. After jazz fusion, they went back to Latin rock for a couple of albums before moving to a generic arena rock sound by the turn of the ‘80s.

In the early ‘80s, Santana began to gain some of its early success back as 1981’s Zebop! was a Top 10 album-hit, their last before Supernatural, and its single “Winning” peaking at #17, their most successful single since “Everybody’s Everything.” “Hold On” from 1982’s Shangó peaked at #15 marking the band’s last major hit before “Smooth.” After that, Santana’s albums for the rest of the ’80s plummeted more and more on the charts with each release. Even a move to Polydor Records in the early ‘90s didn’t help much as their first album for the label, 1992’s Milagro, peaked at a dismal #102. 

While Santana’s albums weren’t selling that much anymore, the band remained a constant live draw. For most acts, this is where the story would end. The band had already become known as one of the defining bands of Woodstock. They didn’t have much else to prove. Santana could have easily spent the rest of their career touring on the oldies circuit continuing to live off of their past glories. Enter Clive Davis.

As head of Columbia Records, Davis had signed Santana to his label in 1969 and oversaw their initial success. This history led Carlos to contact Davis, now head of Arista Records, about making an album to bring him back on top. In their discussions, Carlos talked about wanting his kids to hear him on the radio and in his words “reconnect the molecules with the light” which meant making a radio-friendly album. Davis agreed to the project helping to get Santana out of its contract with Polydor to sign with Arista. To help achieve Carlos’ vision, Davis planned to split Supernatural between each other with half the songs coming from Carlos with the other half, the hits, coming from Davis.

Davis reached out to a bunch of younger contemporary artists to collaborate with Santana and all of them said yes including Dave Matthews, Eagle-Eye Cherry, Everlast, and Lauryn Hill. This was an awfully smart move on Davis’ part considering in its early years of success Santana didn’t have much of an image or frontman. Carlos was obviously the star of the group but he wasn’t the singer and the singing was usually everyone in the band singing together. This type of approach wasn’t going to work in the late ‘90s. And considering the already uphill battle of getting the general public to buy into a long-forgotten Woodstock rocker, getting popular stars of the moment would help him appeal to a younger audience who weren’t alive when Santana first hit it big. This type of approach helped set the blueprint for later era Santana hits. And it all started with “Smooth,” the last song put together for the album.

“Smooth” initially came from industry songwriter Itaal Shur who’s only major credit to that point was writing “Ascension (Don’t Ever Wonder)” which was a Top 10 R&B hit and #36 Hot 100 hit for Maxwell in 1996. Shur’s manager told him about Santana looking for songs for his new album and immediately jumped on board to contribute. After listening to the songs already cut for Supernatural, Shur felt there wasn’t a song on the album that to him represented classic Santana in the vein of their early hits. At his home, Shur arranged a song on his guitar initially called “Room 17” with lyrics originally written about a couple fucking in a hotel room. 

When Shur brought his song to Arista, the label liked the music but felt the lyrics were too sexual. To help polish the song, Arista paired Shur with Rob Thomas, the frontman of the rising rock band Matchbox 20. Growing up in a troubled family, Thomas moved around a lot as a kid before settling with his mom in Orlando, Florida. (The #1 song the week of Thomas’ birth: Nilsson’s “Without You.”) Thomas’ first group, Tabitha’s Secret, played constantly in the Orlando area where they got the attention of record producer Matt Serletic, who had done work with fellow alt-rock group Collective Soul. The band broke up but Thomas along with bassist Brian Yale and drummer Paul Doucette started a new group Matchbox 20. 

With the help of Serletic, Matchbox 20 began attracting the attention of major labels eventually signing to Lava Records, a subsidiary of Atlantic Records. In October 1996, they released their debut album Yourself or Someone Like You which made little impact at first. Slowly but surely, the album started getting regional radio play which spread nationwide pushing the album to #5 on the charts and many of its singles like “3 AM” and “Push” becoming big airplay hits. (They probably would have charted on the Hot 100 had Billboard allowed non-retail singles to chart at the time.) Two other singles “Real World” and “Back 2 Good” were moderate Hot 100 hits. Matchbox 20 were part of a wave of mellow and polished post-grunge bands in the late ‘90s along with acts like the Goo Goo Dolls. By 1999, Matchbox 20 and Rob Thomas weren’t exactly household names but they were being noticed.  

The growing success of the band led Thomas wanting to do some work outside the band. Serletic was in a label deal with Clive Davis and told him about Thomas’ desire for outside projects and to let him know of any. Davis and his team sent them the demo for “Smooth” with Thomas and Shur, who happened to live near each other in Manhattan, working together on the song. While alone in his apartment one day, Thomas began writing lyrics about his then-fiancée, Marisol Maldonado, before meeting up with Shur where they came up with the chorus.

Thomas was not supposed to sing on the final recording. He was just meant to sing on the demo where someone else would sing. Thomas had George Michael in mind for “Smooth” singing the song in his style. When Santana heard the demo, he initially dismissed “Smooth” for being too derivative of his early work. He eventually came around to it when he heard Thomas’ voice liking it so much that he demanded that Thomas record the song with him. After getting permission from Thomas’ label, the two of them recorded “Smooth” together live with the band in three takes with Serletic producing. 

When Arista sent “Smooth” to radio stations, the label sent CDs of the single without Santana’s name on it marking it as “Mystery Artist.” They didn’t want programmers to have any preconceptions of Santana and dismiss them as old news. It’s the same tactic the Bee Gees used on their 1975 #1 “Jive Talkin’.” The song initially took off with adult contemporary stations, who skew older, before catching on with regular Top 40 stations across the country making the song explode beyond every one’s dream. Thomas didn’t even know the song was released as a single until he heard the song blasting out of a passing convertible. You couldn’t ignore it. 

What probably helped with “Smooth’s” blockbuster level success aside from having a frontman of a hot young rising rock group featured is the Latin pop explosion that impacted the charts in 1999. With Latin artists like Ricky Martin, Jennifer Lopez, and Enrique Iglesias hitting #1 throughout the year, the conditions were ripe for a legacy act like Santana to make a comeback. Considering Santana helped lay the groundwork for Latin artists to get mainstream success, the fact that they had their biggest success in the year of the Latin pop explosion is a fun little piece of perfect timing. It also helps that “Smooth” on its own is a pretty awesome jam.

For many, it’s hard to hear “Smooth” with fresh ears considering its massive success in 1999 and its continuing popularity since playing in the background at stores or at major events such as weddings. The amount of overplay has led to a lot of conflicting feelings regarding “Smooth” and Santana’s comeback era. Some hail “Smooth” as a classic and Santana’s greatest creation while others who know Santana’s earlier work dismiss it and Supernatural as a pop sellout that’s nowhere close to his best work. 

Speaking as someone who was barely alive when the song was popular, I agree with both viewpoints. When listening to the drugged-out experimental jams of Woodstock, “Smooth” is definitely not going to rise in comparison. Even Thomas admitted that it’s not his or Santana’s best song. From reviews I’ve heard of Supernatural, it basically amounts to a Now That’s What I Call Music! style compilation with its abundance of collaborations along with your typical solo material from Santana. Not exactly as forward pushing or adventurous as you would expect from the group. You can even argue Supernatural gave birth to the now commonplace collaboration album a la DJ Khaled and Calvin Harris. 

That said, I can’t deny how great of a groove “Smooth” is. Every musician on the song plays at their best and it sounds like they’re having fun. It definitely sounds like it was recorded live in three takes. While it might be Santana playing for the mainstream, there’s still some of that old-style Santana in there with Carlos’ guitar solos echoing the freaked-out nature of the band’s early work which is especially evident on the song’s full five-minute version as well as various live performances. It’s hard not to imagine the band members playing past the song’s length letting the groove direct them wherever. 

As for Thomas, he’s fine. He sings in that typical ‘90s rock singer mold with his grunge-like vocal inflections and enunciations that’s been the butt of a lot of parodies. While his performance isn’t hugely impressive, he brings energy and compliments the fun and sensual nature of the song. On the verses, there’s this weird muffling effect on his voice that enhances his performance like what AutoTune did to Cher’s voice on “Believe.” He has great chemistry with the band where on the outro it sounds like he and Carlos are fighting with each other for who can be the loudest towards the end. 

Lyrically, “Smooth” is a song about loving devotion. Some lines include Latin inspired terms fitting with the music, “My muñequita, my Spanish Harlem Mona Lisa/Out from the barrio, you hear my rhythm from your radio.” Thomas sings about a woman who gives him life, is willing to change himself to accommodate her, and wants to know if this love is real, “Gimme your heart, make it real, or else forget about it.” The lyrics are toned down from its initial lyrics but Rob Thomas still has a sexually charged tone when he sings about this woman. But like with another Latin #1, Ricky Martin’s “Livin’ La Vida Loca,” the lyrics don’t matter much. It’s all about that groove. Production-wise, it holds up remarkably well. Doesn’t sound dated at all maybe outside of Thomas’ vocals. It might be a carefully calculated sell-out move but a great one at that. It’s the perfect summer jam even though it was #1 during the fall and winter.

The music video for “Smooth” also brings home the fun vibe. It shows Rob Thomas and Santana performing both in a shop and on a block party in Manhattan’s Harlem neighborhood for a crowd of happy fans including Thomas’ fiancée. (They would both be married by the time “Smooth” was #1.) Everyone looks like they’re enjoying themselves. Who wouldn’t be dancing along to this?

“Smooth” heavily exceeded everyone’s expectations. It was #1 for the final 11 weeks of 1999 soundtracking the holiday season and Y2K continuing its run for the first week of 2000. This song soundtracked my baptism, my first Halloween, my first Thanksgiving, my first Christmas, and my first New Year’s. Despite most of its run at #1 being in 1999, “Smooth” was more successful in 2000 with Billboard naming it as the #2 single of that year. “Smooth” is also one of the biggest Billboard hits of all time placing 2nd on its recent All-Time Top 100 Songs list behind only Chubby Checker’s #1 hit “The Twist.” The song and the Supernatural album swept the 2000 Grammy Awards with “Smooth” winning Song and Record of the Year and Supernatural winning the coveted Album of the Year award. Considering the Recording Academy’s tendency to reward legacy acts, that’s not surprising. 

The success of “Smooth” wasn’t a fluke as Santana scored another massive #1 hit in April 2000 with “Maria Maria” featuring The Product G&B. (It’s a 6.) Santana wouldn’t get back to #1 but lasted a little longer on the charts netting his final Top 10 hit in 2003 with “Why Don’t You & I” featuring Alex Band of The Calling and it peaked at #8. (It’s also a 6.) The comeback eventually faded as Santana went back to touring the oldies circuit where they continue to perform and release new albums. Carlos Santana was also awarded the Kennedy Center Honors in 2013. As bandleader, Carlos Santana is, as far as I know, the last artist ever to top the Hot 100 who’s older than the chart itself. 

Rob Thomas would continue as frontman for Matchbox 20 where they would spend the next few years churning out a steady stream of hits including their only #1 “Bent” which hit the top spot shortly after “Smooth” in July 2000. (It’s a 6.) Thomas would eventually go out on his own netting moderate success in the mid to late 2000s with one other Top 10 hit in 2005 with “Lonely No More,” a funky pop jam and it peaked at #6. (It’s a 7.) Thomas still tours with Matchbox 20 where he alternates between band and solo albums. 

“Smooth” isn’t going away. It’s going to be with us long after we’re all dead. For the last #1 of my birth year, I couldn’t be happier to end it with “Smooth.” 

GRADE: 9/10

BONUS BEATS: In 2013, the comedy video channel Funny or Die released a cop show parody based on “Smooth” with Rob Thomas reciting the lyrics. Here’s the video:

BONUS BONUS BEATS: Here’s a personal one of mine. Last year for my birthday, me and a couple of friends covered “Smooth.” It’s not that great but we did our best. Here’s the video: