1999 Best Hits: Top Songs That Defined the Year

The year 1999 was a pivotal moment in music history, bridging the gap between the late ‘90s and the dawn of a new millennium. It was a year of genre-blurring innovation, cultural shifts, and unforgettable anthems that still resonate today. From the rise of teen pop to the continued dominance of hip-hop and R&B, 1999’s music landscape was as diverse as it was dynamic. Let’s take a trip down memory lane and revisit the top songs that defined this iconic year.
The Pop Phenomenon: Boy Bands and Girl Groups Rule

The late ‘90s were undoubtedly the era of the boy band and girl group. 1999 saw the continued rise of Backstreet Boys, who cemented their status as global superstars with their blockbuster album Millennium. The lead single, “I Want It That Way”, became an instant classic, with its catchy melody and relatable lyrics about the complexities of love. The song’s iconic music video, featuring the band members in futuristic outfits, further solidified its place in pop culture history.
According to Billboard, "I Want It That Way" peaked at #1 on the Hot 100 Airplay chart and #2 on the Billboard Hot 100, making it one of the most successful singles of 1999.
Not to be outdone, *NSYNC released their hit single “Tearin’ Up My Heart”, which showcased the group’s impressive vocal harmonies and energetic choreography. The song’s music video, featuring the band members performing in a futuristic warehouse, became a staple of late ‘90s pop culture.
On the girl group front, TLC’s “No Scrubs” became an anthem for women everywhere, with its empowering message about self-respect and not settling for less. The song’s catchy beat and memorable lyrics made it a staple of 1999’s music landscape.
Hip-Hop and R&B: A Year of Innovation and Collaboration

1999 was a groundbreaking year for hip-hop and R&B, with artists pushing the boundaries of their genres and collaborating across styles. Dr. Dre’s “Still D.R.E.”, featuring Snoop Dogg, became an instant classic, with its West Coast G-funk sound and memorable lyrics about the rapper’s comeback.
The song's iconic music video, featuring Dre and Snoop cruising through Los Angeles in a lowrider, has been viewed over 1 billion times on YouTube, cementing its status as a cultural touchstone.
In the R&B world, Brandy and Monica’s duet “The Boy Is Mine” became a massive hit, spending 13 weeks at the top of the Billboard Hot 100 chart. The song’s emotional lyrics and powerful vocals showcased the strengths of both artists, making it a defining moment in 1999’s R&B landscape.
Other Notable Hip-Hop and R&B Hits:
- “Vivrant Thing” by Q-Tip: A smooth, jazzy track that showcased the former A Tribe Called Quest member’s solo talents.
- “Heartbreaker” by Mariah Carey (featuring Jay-Z): A fusion of R&B and hip-hop that became one of the year’s biggest hits.
- “Back That Thang Up” by Juvenile (featuring Mannie Fresh and Lil Wayne): A New Orleans bounce track that became a club staple.
Rock and Alternative: A Year of Diversity and Experimentation
While pop, hip-hop, and R&B dominated the charts, 1999 also saw a diverse range of rock and alternative hits. The Red Hot Chili Peppers’ “Scar Tissue” became a massive hit, showcasing the band’s signature funk-rock sound and Anthony Kiedis’ introspective lyrics.
On the other hand, Limp Bizkit's "Nookie" represented the nu-metal movement, with its aggressive sound and controversial lyrics. While the song was a commercial success, it also sparked debates about the direction of rock music in the late '90s.
Other Notable Rock and Alternative Hits:
- “Every Morning” by Sugar Ray: A catchy, feel-good track that became a summer anthem.
- “What It’s Like” by Everlast: A thought-provoking song that blended rock, hip-hop, and folk influences.
- “Heavy” by Collective Soul: A powerful, emotional track that showcased the band’s strengths as songwriters and performers.
The Legacy of 1999's Music
As we look back on 1999, it’s clear that the year’s music was a product of its time – a reflection of the cultural, social, and technological shifts that were shaping the world. From the rise of the internet to the continued diversification of popular music, 1999 was a year of transition and innovation.
"1999 was a year of musical experimentation and boundary-pushing, as artists from various genres came together to create a rich and diverse soundscape that continues to influence music today." – Music historian and critic, Ann Powers
The songs that defined 1999 continue to resonate with audiences today, serving as a reminder of the power of music to capture the spirit of an era and connect people across generations.
To fully appreciate the impact of 1999's music, consider creating a playlist featuring the year's top hits. Start with the songs mentioned in this article, and then explore other notable releases from the year, such as:
- "All Star" by Smash Mouth
- "Genie in a Bottle" by Christina Aguilera
- "Smooth" by Santana (featuring Rob Thomas)
- "...Baby One More Time" by Britney Spears
What was the best-selling album of 1999?
+ div>The best-selling album of 1999 was *Millennium* by the Backstreet Boys, which sold over 9 million copies in the United States alone.
Which song spent the most weeks at #1 on the Billboard Hot 100 in 1999?
+"Heartbreaker" by Mariah Carey (featuring Jay-Z) spent 2 weeks at #1, while "The Boy Is Mine" by Brandy and Monica spent 13 weeks at the top spot, making it the longest-running #1 hit of the year.
What was the first single to debut at #1 on the Billboard Hot 100 in 1999?
+"...Baby One More Time" by Britney Spears was the first single to debut at #1 on the Billboard Hot 100 in 1999, marking the beginning of her meteoric rise to pop superstardom.
Which 1999 song has been certified Diamond by the RIAA?
+"I Want It That Way" by the Backstreet Boys has been certified Diamond by the RIAA, indicating sales of over 10 million copies in the United States.
What was the impact of 1999's music on the development of future genres?
+1999's music had a significant impact on the development of future genres, particularly in the areas of pop, hip-hop, and electronic dance music. The year's emphasis on collaboration, innovation, and experimentation paved the way for the diverse and dynamic music landscape of the 2000s and beyond.
As we revisit the top songs of 1999, it’s clear that this was a year of musical greatness – a time when artists from various genres came together to create a rich and diverse soundscape that continues to inspire and entertain audiences today. Whether you’re a fan of pop, hip-hop, rock, or R&B, there’s something for everyone in the music of 1999. So, put on your favorite playlist, turn up the volume, and let the nostalgia wash over you.