Best Hits of 1999: 10 Iconic Songs That Still Rock

When 1999 burst onto the music scene, it left a lasting legacy of chart‑topping tracks that still echo in radio stations, playlists, and memories. From pop anthems to rock ballads, these songs shaped a generation and remain cultural touchstones. In this guide, we dive deep into the best hits of 1999, exploring the stories behind each track, chart performance, and why they continue to resonate.

Why 1999 Was a Music Milestone

1999 marked the peak of the late‑90s pop boom, with digital downloads beginning to reshape how fans accessed music. The year saw the ascent of iconic artists who defined the soundscape for years to come. Understanding this context helps explain why the best hits of 1999 still dominate playlists.

Chart‑Dominating Numbers

According to Billboard, 1999 produced 20 singles that reached the top 10, a record for the decade. Six of those songs hit number one, an unprecedented concentration of hits in a single year. These statistics underscore the commercial potency of the era.

Streaming Revivals

On Spotify, tracks like “…Baby One More Time” and “I Want It That Way” have amassed over 1.5 billion streams each, proving their timeless appeal. Streaming data reveals a 30% increase in 2024 for songs released in 1999, indicating strong generational crossover.

How to Curate a 1999‑Themed Playlist for 2024

Building a playlist that captures the essence of 1999 requires mixing genres, tempos, and moods. Below are actionable steps to create a nostalgic yet fresh listening experience.

1. Start with the hits. Include the five number‑one singles to anchor the playlist.
2. Balance energy. Alternate high‑tempo pop tracks with slower rock ballads to maintain flow.
3. Layer deep cuts. Add lesser‑known tracks like “Holland, 1945” to surprise listeners.
4. Use streaming analytics. Platforms such as Spotify’s “Year in Review” show which songs have the highest weekly streams.
5. Tag with era‑specific phrases. Use tags like “90s nostalgia” or “1999 hits” to boost discoverability.

Actionable Insights for Music Curators

Curating music isn’t just about picking popular songs; it’s about storytelling. Here are concrete tactics for maximizing engagement.

• Theme each segment. Group songs by sub‑genre (e.g., “Pop Powerhouses,” “Rock & Alternative”) to create narrative arcs.
• Highlight collaborations. Spotlight tracks featuring multiple high‑profile artists to trigger cross‑audience interest.
• Incorporate visual media. Pair tracks with 1999‑era music videos or lyric videos for a richer experience.
• Leverage social media challenges. Encourage users to create dance videos to songs like “Bye Bye Bye” to drive engagement.

Key Takeaways for 2024 Music Lovers

Even decades later, the best hits of 1999 continue to set production standards and inspire new artists. Their catchy hooks, polished production, and cultural relevance make them perfect for themed events, nostalgia playlists, and music education.

By combining data‑driven insights with creative curation, you can craft playlists that resonate with both longtime fans and new listeners. Dive in, hit play, and let 1999’s iconic sounds shape your next listening session.

1999’s Pop Powerhouses: The Top 5 Chart‑Dominating Hits

1999 was a golden year for pop music, creating a soundtrack that still feels fresh today. The five singles below became cultural touchstones, each breaking records on the Billboard Hot 100 and forever altering the pop landscape.

Britney Spears – “…Baby One More Time”

Britney’s debut single catapulted her into worldwide fame, holding the number one spot for 10 consecutive weeks. The track sold 1.8 million copies in the U.S. alone during its first week, a record for a debut single at the time.

Actionable Insight: When curating a 1999 playlist, start with this anthem to instantly set the nostalgic tone. Pair it with songs that also topped the charts in that era for a seamless listening experience.

Data Point: The single earned Britney her first Grammy nomination for Best New Artist and was certified 5× Platinum by the RIAA.

Backstreet Boys – “I Want It That Way”

A timeless ballad that remains a karaoke staple, praised for its emotive melody and soaring vocal harmonies. The song peaked at number one in 15 countries, showcasing its global appeal.

Actionable Insight: Use this track as the emotional midpoint in a playlist. Its 4:12 runtime balances the high energy of earlier hits with the slower tracks that follow.

Stat Highlight: The single sold 3.2 million copies worldwide in its first year, making it the best‑selling single of 1999 in the U.K.

NSYNC – “Bye Bye Bye”

A high‑energy track that showcased the group’s signature harmonies and guitar riffs. The song stayed on the Billboard Hot 100 for 32 weeks, a testament to its enduring popularity.

Actionable Insight: Include “Bye Bye Bye” as a dance floor booster. Its 98 bpm tempo is ideal for playlist loops in party or workout settings.

Statistic: The music video, directed by Dave Meyers, amassed 17 million views within the first month of its 1999 release, setting a new YouTube milestone for the era.

Christina Aguilera – “Genie in a Bottle”

Aguilera’s sultry debut single topped charts across continents, reaching number one in the U.S., Canada, and Australia. The track’s hook “I got a bad habit, crave you like a …” became instantly recognizable.

Actionable Insight: Use “Genie in a Bottle” to bridge pop and R&B flavors in a playlist. Its 90 bpm groove fits well with contemporary pop songs, ensuring cross‑generational appeal.

Data Point: The single earned Aguilera her first Grammy win for Best Female Pop Vocal Performance in 2000, solidifying her position as a pop icon.

Shakira – “Whenever, Wherever”

A cross‑cultural hit that blended Latin rhythms with mainstream pop appeal. The song broke into the top five in 13 countries, including the U.S., U.K., and Brazil.

Actionable Insight: Position this track at the end of a playlist to leave listeners with a high‑energy, world‑music vibe. Its 91 bpm tempo keeps the energy up while showcasing Shakira’s signature hips.

Statistic: “Whenever, Wherever” earned Shakira her first Billboard Latin Music Award for “Latin Pop Airplay Song of the Year,” highlighting its crossover success.

Why These Hits Still Matter

Each track exemplifies a key trend from 1999: polished pop production, global crossover appeal, and the rise of digital media. Their continued streaming numbers—over 1 billion combined streams on Spotify—attest to their timelessness.

Actionable Insight: When building a 1999‑themed playlist, aim for a balance of high‑chart hits and genre‑diverse tracks. Include short interludes of 30‑second clips from iconic 1999 commercials to enhance the nostalgic feel.

Stat Highlight: According to Spotify’s “Year in Review 2023,” the combined monthly listeners for these five songs exceed 45 million, proving that 1999’s pop powerhouses still resonate with modern audiences.

Rock & Alternative Icons: Songs That Defined the Grunge Revival

In 1999, while pop dominated the top of the charts, rock and alternative acts pushed creative limits, offering listeners deeper, more complex sounds.

Radiohead – “Karma Police”

This track, released as the lead single from *OK Computer*, showcased Radiohead’s signature blend of atmospheric guitars and introspective lyrics.

Chart data shows the song peaked at #4 on the Billboard Hot 100 and remained on the chart for 21 weeks.

Actionable Insight: For playlist curators, “Karma Police” pairs well with other 1999 alt‑rock staples like Nine Inch Nails’ “The Hand That Feeds” or Foo Fighters’ “All My Life.”

Data Point: The single sold 1.5 million copies in the U.S. and earned a gold certification from the RIAA.

Keyword Focus: “best rock songs 1999” is highlighted by radio airplay and streaming numbers, making this track indispensable for any 1999 rock compilation.

Red Hot Chili Peppers – “Scar Tissue”

“Scar Tissue” fused funk grooves with melodic rock, becoming a signature track for the band during the late‑90s tour circuit.

It peaked at #2 on the Billboard Hot 100 and stayed on the chart for 25 weeks, selling an estimated 1.5 million copies.

Actionable Insight: Pair “Scar Tissue” with acoustic tracks like Counting Crows’ “A Long December” to create an energetic yet emotionally resonant playlist.

Data Point: The music video accrued over 3 million views on YouTube by 2008, reflecting its lasting popularity.

Keyword Focus: “alternative music 1999” and “rock hits 1999” both rank high for this song when users search for top‑charting tracks.

Neutral Milk Hotel – “Holland, 1945”

Although not a mainstream hit, “Holland, 1945” became a cult anthem within indie circles, celebrated for its poetic storytelling.

The track peaked at #15 on the Billboard Alternative Songs chart and is a staple on indie classic playlists.

Actionable Insight: For niche curators, include “Holland, 1945” alongside Pavement’s “Cut Your Hair” to capture the lo‑fi ethos of 1999’s underground scene.

Data Point: The song has over 12 million streams on Spotify as of 2024, a testament to its enduring appeal.

Keyword Focus: “indie gem 1999” and “cult classic rock 1999” are strategic tags for niche audiences seeking non‑mainstream tracks.

Other Notable 1999 Rock Staples

• Foo Fighters – “All My Life”: Reached #3 on the Billboard Hot 100; 1.8 million U.S. sales.
• Green Day – “Minority”: #8 on the Billboard Hot 100; sold 2 million copies.
• REM – “The Day.”: #4 on the Billboard alternative chart; 250,000 U.S. sales.

How to Curate a 1999 Rock Playlist

1. Start with chart‑topper leads like “Karma Police” and “Scar Tissue.”
2. Add deep cuts—“Holland, 1945” showcases indie depth.
3. Balance high‑energy tracks with mid‑tempo songs for dynamic flow.
4. Utilize streaming data: Spotify’s “Top 50 – Global” for 1999 can surface hidden gems.

By blending mainstream successes with cult favorites, you’ll craft a playlist that reflects the full spectrum of the grunge revival and alt‑rock movement of 1999.

Hip‑Hop & R&B Highlights: Beats That Set the Tone

1999’s hip‑hop and R&B landscape was a melting pot of gritty storytelling, smooth vocal runs, and production that still sounds fresh today. Fans remember the year for its bridge between underground grit and radio‑friendly hits, a trend that set the stage for modern pop‑rap.

Dr. Dre – “The Next Episode”

Released as the lead single from 2001, “The Next Episode” showcased Dre’s signature funk‑laden synth lines and Snoop Dogg’s laid‑back flow. The track peaked at #5 on the Billboard Hot 100 and sold over 1 million copies in the U.S., earning a Platinum certification from the RIAA.

Actionable insight for producers: layer a crisp 808 kick with a melodic synth hook, then let a vocal sample sit in the background to create that classic West Coast groove. DJs can spin this track by easing into the bassline during a warm‑up set to build instant crowd energy.

• Use a high‑pass filter on the vocal sample to keep the low‑end punchy.
• Drop a short “G-Funk” bridge around the 1:15 mark for a surprise hook.
• Incorporate a live guitar riff in a remix to modernize the feel.

Mary J. Blige – “No More Drama”

Mary J. Blige’s 1999 anthem “No More Drama” blended her gospel‑infused vocal power with a hard‑hitting beat. The single debuted at #16 on the Hot 100 and climbed to #4 on the R&B/Hip‑Hop chart, staying on the Billboard charts for 22 weeks.

Statistical highlight: the track amassed over 1.7 million sales, earning a Platinum certification in 2000. Its chorus—“I’m not gonna let you get me down”—became a cultural phrase, frequently sampled in later R&B productions.

For remixers, keep the vocal hook intact and experiment with a syncopated trap snare pattern to appeal to younger audiences. Spotify playlist curators can slot this track into “90s R&B Essentials” for optimal discoverability.

• Layer a subtle pad behind the vocal to add depth.
• Use side‑chain compression on the kick to maintain punch in a remix.
• Drop a vocal chop at 2:05 for an unexpected hook.

Jay‑Z – “Still D.R.E.” (Remix)

The 1999 remix of “Still D.R.E.” featured Jay‑Z’s sharp lyricism over Dr. Dre’s polished production, cementing the track’s status as a hip‑hop staple. The single reached #3 on the Hot 100 and held the #1 spot on the R&B/Hip‑Hop chart for six consecutive weeks.

Data point: the remix sold 1.5 million units in the U.S. alone, earning a 2× Platinum certification. Its hook—“Still a G‑f—” became synonymous with longevity in the rap world, influencing artists like Kendrick Lamar and Nick i Minaj.

Actionable tip: mix the vocal tracks on separate stems to allow for creative remixing; this technique enables remixers to emphasize Jay‑Z’s flow or Dr. Dre’s synths independently.

• Apply a subtle delay on the vocal at the chorus for added atmosphere.
• Use a high‑end boost on the synth line to make the track stand out in club settings.
• Consider a vinyl‑style crackle overlay for nostalgic remix vibes.

By studying the production tricks, chart performance, and remix potential of these 1999 classics, modern DJs and producers can harness the era’s timeless energy while adding their own contemporary flair.

1999 Music Trends: A Data‑Driven Comparison Table

Below is an HTML table summarizing key metrics for the top 10 songs of 1999, including peak chart positions, weeks on chart, and sales figures.

Song	Artist	Peak Billboard Rank	Weeks on Chart	Estimated Sales (Millions)
…Baby One More Time	Britney Spears	#1	35	3.5
I Want It That Way	Backstreet Boys	#1	33	2.8
Bye Bye Bye	NSYNC	#3	29	1.9
Genie in a Bottle	Christina Aguilera	#2	30	2.2
Whenever, Wherever	Shakira	#3	28	2.0
Karma Police	Radiohead	#4	21	0.8
Scar Tissue	Red Hot Chili Peppers	#2	25	1.5
Holland, 1945	Neutral Milk Hotel	#15	3	0.1
The Next Episode	Dr. Dre	#5	20	1.2
No More Drama	Mary J. Blige	#4	22	1.7

Key Takeaways for 1999 Music Trends

Analyzing the table reveals that pop dominated the charts, with three songs hitting number one. This trend underscores the genre’s commercial power in the late 90s.

Britney Spears’ “…Baby One More Time” led the pack with 3.5 million units sold, a benchmark for pop singles that many contemporary artists still aspire to reach.

Backstreet Boys’ “I Want It That Way” followed closely, selling 2.8 million copies and spending 33 weeks on the Hot 100. This longevity demonstrates the importance of sustained radio play.

“Karma Police” by Radiohead, while lower on the Billboard ranking, sold 0.8 million copies—highlighting how critical acclaim can translate into solid sales even outside the pop domain.

Actionable Insights for Modern Playlist Curators

Use the weekly chart data to cycle genres: start with a high‑tempo pop hit, drop into a rock anthem, and finish with an R&B ballad.

• For a nostalgic party, place “…Baby One More Time” first to capture instant recognition.
• Insert “Scar Tissue” mid‑playlist to shift energy while maintaining mainstream appeal.
• End with “No More Drama” to leave listeners humming a powerful hook.

When building a streaming playlist, aim for a spread of at least 5–7 unique top‑10 songs from 1999 to mirror the era’s diversity.

Leveraging Data for Marketing Campaigns

Marketers can target 1999 nostalgia by emphasizing sales milestones in ad copy—e.g., “over 3 million copies sold.”

1. Highlight the “35 weeks” tenure of “…Baby One More Time” to illustrate its staying power.
2. Showcase “Bye Bye Bye”’s 29‑week chart run to appeal to fans of teen pop.
3. Use the 0.8 million sales of “Karma Police” to attract indie rock enthusiasts.

These data points provide concrete proof of each track’s impact, boosting credibility in marketing narratives.

Future-Proofing 1999‑Inspired Content

Incorporate 1999 sales figures into year‑in‑review articles or comparison posts about today’s streaming numbers.

For instance, compare “…Baby One More Time”’s 3.5 million physical sales to its current Spotify streams, which surpass 1.2 billion—showing the shift from ownership to access.

Tracking such trends helps music educators and historians contextualize the evolution of consumption habits.

FAQs Revisited with Data Context

When answering “Which artist had the most number‑one hits in 1999?” reference the table’s peak ranks: both Britney Spears and Backstreet Boys secured the top spot.

For “Did any 1999 songs win major awards?” note that “I Want It That Way” received a Grammy for Best Pop Performance by a Duo or Group, aligning with its commercial success.

These data-driven answers deepen reader trust and enrich the article’s authority.

Expert Tips: How to Curate a 1999‑Themed Playlist

Curating a playlist that truly captures the sonic vibe of 1999 is both an art and a science. By blending genre icons, tempo dynamics, and data‑driven choices, you can create a listening journey that feels authentic to the year.

1. Start with a Genre Blueprint

Map out the core genres that defined 1999: pop, rock, hip‑hop, and R&B. This ensures your playlist reflects the era’s diversity.

• Pop gems like “…Baby One More Time” and “Whenever, Wherever” anchor your list.
• Rock staples such as “Karma Police” and “Scar Tissue” add depth.
• Hip‑hop hits like “The Next Episode” bring street credibility.
• R&B bangers including “No More Drama” complement the mix.

Using this framework, avoid over‑loading one genre and keep the flow balanced.

2. Tempo & Energy: The Pulse of Your Playlist

Tempo variation keeps listeners engaged. Aim for a 1:1 ratio of high‑energy tracks to slower ballads.

1. Start with an upbeat opener: “Bye Bye Bye” (≈120 bpm) sets a lively tone.
2. Insert a mid‑tempo rocker: “Scar Tissue” (≈90 bpm) offers a mellow break.
3. Follow with a radio‑friendly pop: “Genie in a Bottle” (≈95 bpm).
4. Drop a soulful R&B slow‑jam: “No More Drama” (≈84 bpm).

Use the SongBPM tool to verify beats per minute for each track.

3. Leverage Streaming Analytics for Authenticity

Data-backed choices give your playlist credibility. Spotify’s “Year in Review” and Apple Music’s “Most Streamed 1999” charts reveal listener favorites.

• Spotify: Search “1999 Year in Review” to find top‑streamed tracks, confirming hits like “…Baby One More Time” at 3.5 m streams.
• Apple Music: Explore the “Top 1999” playlist, where “I Want It That Way” ranks consistently #2.
• Chart correlation: Verify Billboard peak positions align with streaming data for authenticity.

Incorporate at least 70% of the top‑streamed songs to mirror the era’s popularity.

4. Add Hidden Gems for Depth

While chart‑busters drive recognition, underground tracks showcase 1999’s underground scene.

• Feature “Holland, 1945” (Neutral Milk Hotel) for indie flair.
• Insert “Lonely” by The Veronicas (released 1999) for a lesser‑known pop touch.
• Drop a funk‑rap hybrid: “Gettin’ Up” by 2Pac.

Hidden gems keep the playlist fresh and cater to die‑hard fans.

5. Use Thematic Transitions

Smooth transitions maintain momentum. Pair songs with similar key signatures or vocal styles.

1. Link “Genie in a Bottle” (key of A major) to “Whenever, Wherever” (A major) for harmonic continuity.
2. Bridge “Karma Police” (E minor) with “Scar Tissue” (E minor) to preserve mood.
3. End with an uplifting anthem: “I Want It That Way” (C major) to close on a high note.

Use streaming platform features like “Crossfade” to blend tracks seamlessly.

6. Final Checklist Before Publishing

Ensure your playlist meets these criteria:

• Minimum of 25 tracks to cover breadth.
• Genre spread: 30% pop, 25% rock, 25% hip‑hop, 20% R&B.
• Inclusion of at least two top‑streamed hits per genre.
• Balanced O A tempo ratio: 12 uptempo, 13 ballads.
• All tracks released between Jan 1 1999 and Dec 31 1999.

Once satisfied, share the playlist on Spotify, Apple Music, and social media with a catchy description like “Relive the roar of 1999 – the ultimate 25‑track throwback collection.”

These actionable steps, backed by concrete data, will help you craft a playlist that not only sounds great but also feels like a time capsule for anyone who lived through 1999.

Frequently Asked Questions About 1999 Music

What were the top 10 singles of 1999?

The year’s chart‑topping 10 included “…Baby One More Time,” “I Want It That Way,” and “Bye Bye Bye.”

Other entries were “Genie in a Bottle,” “Whenever, Wherever,” and “Karma Police.”

These tracks dominated the Billboard Hot 100, each spending 20+ weeks in the top 10.

Collectively, they sold over 30 million copies worldwide.

Which artist had the most number‑one hits in 1999?

Britney Spears claimed two number‑ones: “…Baby One More Time” and “…Sometimes.”

The Backstreet Boys matched her with “I Want It That Way” and “Show Me.”

Both acts stayed on the top spot for a combined 15 weeks.

This dual dominance cemented 1999 as a peak year for pop boybands.

Did any 1999 songs win major awards?

Yes, the Backstreet Boys earned the 2000 Grammy for Best Pop Performance by a Duo or Group.

Britney Spears received a Billboard Music Award for Top Hot 100 Artist.

Radiohead’s “Karma Police” won a 2000 NME Award for Best Track.

These accolades underscore the year’s crossover appeal.

What was the most streamed 1999 song on Spotify?

“…Baby One More Time” tops Spotify’s 2024 “1999 Hits” playlist with 1.2 billion streams.

It ranks #3 among all‑time most‑streamed songs from 1999 on the platform.

The track’s upbeat hook keeps it relevant for millennials and Gen Z alike.

Its streaming count is 30% higher than the second‑place hit.

How did 1999 influence modern pop music?

The year popularized hook‑centric songwriting, a template used by artists like Ariana Grande.

Polished production values set the standard for today’s pop ballads.

Song structures from 1999—verse‑pre‑chorus‑chorus—are still taught in contemporary songwriting courses.

Digital remastering of 1999 tracks boosts their clarity for modern listeners.

Which 1999 rock song is considered the best?

Radiohead’s “Karma Police” is often cited as the pinnacle of 1999’s rock landscape.

The track peaked at #4 on the Billboard Hot 100 and #1 on the Modern Rock chart.

Its sales exceed 2 million units worldwide.

Critics praise its atmospheric guitar and introspective lyrics.

Was 1999 a significant year for hip‑hop?

Absolutely; Dr. Dre’s “The Next Episode” exemplified West Coast rap’s mainstream breakthrough.

It spent 20 weeks in the top 10 and sold 1.2 million copies.

Jay‑Z’s “Still D.R.E.” remix further solidified hip‑hop’s presence on pop radio.

These tracks influenced the sound of 2000s hip‑hop production.

Are there any 1999 songs that are still popular today?

Many tracks, like “I Want It That Way,” remain staples in playlists and films.

They regularly feature in TikTok challenges and nostalgic ads.

Streaming numbers for “…Baby One More Time” surpass 1 billion across all platforms.

These songs continue to generate new revenue streams for artists.

How can I find 1999 music on streaming platforms?

Search “1999 hits” or “best songs of 1999” on Spotify, Apple Music, or YouTube Music.

Look for official playlists curated by the platforms or fan communities.

Use the “Year in Review” feature on Spotify for curated 1999 collections.

Don’t forget to explore “Throwback Thursday” playlists on Apple Music.

What 1999 song is best for a nostalgic party?

“Bye Bye Bye” by NSYNC is a guaranteed crowd‑pleaser at themed events.

Its high‑energy beat encourages dancing and sing‑alongs.

It holds a 30‑minute spot in most “90s party” mixes.

Pair it with “…Baby One More Time” for a dynamic setlist.

Conclusion

Remembering the best hits of 1999 feels like stepping onto a well‑tuned stage that’s still echoing today. The year’s chart‑dominating pop anthems and gritty rock tracks continue to influence modern playlists and radio rotations.

Here’s how you can turn that nostalgia into a tangible listening experience:

1. Build a 1999‑Themed Playlist in Minutes

   Open Spotify, Apple Music, or YouTube Music and search “1999 hits.” The platform will auto‑suggest a ready‑made playlist filled with chart‑toppers like “…Baby One More Time” and “Karma Police.”

   To personalize, add at least 15 tracks from the article’s top‑10 list, then sprinkle in hidden gems such as “Holland, 1945” or “Scar Tissue.”

2. Use Data to Fine‑Tune Your Mix

   According to the article’s table, Britney’s single sold an estimated 3.5 million copies in 1999. Pair that high‑sales track with a low‑chart band like Neutral Milk Hotel to balance nostalgia and underground appeal.

   Downloads and streams can be cross‑checked on Billboard’s Year‑End charts or Official Charts.

3. Create a Theme‑Based Listening Party

   Invite friends for a “90s Throwback” night. Divide the playlist into four segments: pop, rock, hip‑hop, and R&B. Play a trivia quiz after each segment to keep the energy high.

   Use the article’s facts—like Dr. Dre’s “The Next Episode” topping the R&B charts—to prompt discussion.

4. Both Spotify and Apple Music provide “Year in Review” sections. Compare 1999’s streaming totals to other years to see how these hits rank today.

   For instance, “I Want It That Way” currently has over 1.2 billion streams on Spotify, a staggering number that shows its lasting appeal.

5. Share a collage of 1999 album covers (like the one in the article) on Instagram or Pinterest. Use the alt text “1999 music album covers” for SEO value.

   Tag relevant hashtags: #1999Hits, #90sMusic, #RetroPlaylist.

   Beyond the data, the emotional resonance of these tracks fuels countless moments—from high school dances to moment‑of‑clarity karaoke sessions. They’re more than just songs; they’re touchstones that remind us of late‑night mixtapes and first‑time dance moves.

   So grab your headphones, hit play, and let the best hits of 1999 transport you back to a pivotal year in music history.