The Top 101 Songs from 1999 (with Spotify Playlist)

Songs from 1999?

Oh, buckle up for a trip down memory lane!

Remember when the internet took ages to load and Y2K had us all on edge?

But hey, it was also the era of catchy tunes and iconic styles.

Picture this: boy bands with frosted tips, cargo pants, and butterfly clips. Yep, that’s the vibe.

The Billboard Year-End Hot 100 and other charts give us a peek into the musical magic of that era.

From Cher’s iconic “Believe” (cue the auto-tune magic) to TLC’s sassy “No Scrubs,” these songs weren’t just chart-toppers; they were the anthems of our lives.

Let’s dive into the time capsule and groove like it’s 1999!

And, if you’re eager to start the nostalgia trip, just hit play on this Spotify playlist and let the memories flood back!

1. “Believe” by Cher

Cher’s “Believe” marked her triumphant return to the music scene, becoming a defining anthem of resilience and empowerment.

Its pioneering use of Auto-Tune created a distinctive sound, propelling it to the top of the charts worldwide.

2. “No Scrubs” by TLC

TLC’s “No Scrubs” delivered a bold message of self-respect and independence, striking a chord with listeners globally.

Its infectious beat and catchy lyrics made it a staple of late-’90s pop culture.

Whether cruising with friends or asserting your worth, this song is the ultimate empowerment anthem.

3. “Angel of Mine” by Monica

Monica’s “Angel of Mine” is a soulful ballad that beautifully captures the feeling of love and devotion.

Its heartfelt lyrics and emotive vocals resonated deeply with audiences, earning it a place among the era’s classics.

4. “Heartbreak Hotel” by Whitney Houston featuring Faith Evans and Kelly Price

Whitney Houston’s rendition of “Heartbreak Hotel” showcased her unparalleled vocal prowess, backed by the soulful harmonies of Faith Evans and Kelly Price.

This song captures the sadness of losing love, making it perfect for times when you’re reflecting or trying to heal.

5. “…Baby One More Time” by Britney Spears

Britney Spears burst onto the music scene with “…Baby One More Time,” a pop sensation that captivated audiences worldwide.

Its catchy melody and unforgettable chorus made it an instant classic.

Whether reliving your teenage years or embracing nostalgia, this song remains a quintessential part of the ’90s era.

6. “Kiss Me” by Sixpence None the Richer

Sixpence None the Richer’s “Kiss Me” enchanted listeners with its dreamy acoustic sound and romantic lyrics.

This timeless love song captured the essence of youthful romance, making it perfect for intimate moments or lazy afternoons spent with loved ones.

7. “Genie in a Bottle” by Christina Aguilera

Christina Aguilera’s debut single “Genie in a Bottle” showcased her powerhouse vocals and undeniable charisma.

Its infectious rhythm and playful lyrics dominated the charts, solidifying Aguilera’s status as a pop icon.

8. “Every Morning” by Sugar Ray

Sugar Ray’s “Every Morning” is a breezy, feel-good anthem that captures the carefree spirit of the late ’90s.

Its catchy hooks and laid-back vibe make it perfect for road trips or lazy days at the beach.

With its infectious energy, this song never fails to lift the mood.

9. “Nobody’s Supposed to Be Here” by Deborah Cox

Deborah Cox’s powerful vocals shine in “Nobody’s Supposed to Be Here,” a soulful R&B ballad about unexpected love.

Its emotional depth and soaring chorus resonated with listeners, earning it a place atop the charts.

10. “Livin’ la Vida Loca” by Ricky Martin

In 1999, Ricky Martin’s “Livin’ la Vida Loca” ignited dance floors with its infectious Latin rhythms and irresistible energy.

This iconic anthem perfectly captured the spirit of living life to the fullest, earning Martin worldwide recognition.

11. “Where My Girls At?” by 702

702’s “Where My Girls At?” is a fierce anthem celebrating female camaraderie and solidarity.

Its catchy beat and empowering lyrics resonated with audiences, making it a staple of girl-power playlists.

12. “If You Had My Love” by Jennifer Lopez

Jennifer Lopez’s debut single “If You Had My Love” introduced her as a powerhouse vocalist and style icon.

Its sultry melody and heartfelt lyrics explored themes of trust and vulnerability, resonating with audiences worldwide.

13. “Slide” by Goo Goo Dolls

Goo Goo Dolls’ “Slide” is a melodic rock anthem that captures the bittersweet beauty of love and loss.

Its poignant lyrics and infectious melody struck a chord with listeners, earning it a place among the era’s most beloved ballads.

Whether reminiscing about past relationships or seeking solace in music, this song provides comfort in times of heartache.

14. “Have You Ever?” by Brandy

Brandy’s “Have You Ever?” from ’99 is a soulful ballad that hits deep.

With its haunting melody and emotive vocals, it’s all about longing and regret.

If you’ve felt the sting of unrequited love, this song speaks to your soul and offers solace in emotional turmoil.

15. “I Want It That Way” by Backstreet Boys

Backstreet Boys’ “I Want It That Way” is undeniably one of the standout songs from 1999, a pop masterpiece that defined an era with its infectious melody and unforgettable chorus.

Its timeless appeal transcends generations, making it a karaoke favorite and a staple of ’90s nostalgia playlists.

16. “I’m Your Angel” by R. Kelly and Celine Dion

R. Kelly and Celine Dion’s duet “I’m Your Angel” is a soulful ballad that celebrates the power of unconditional love.

Their emotive vocals and heartfelt lyrics resonate deeply, making it a popular choice for weddings and romantic occasions.

17. “All Star” by Smash Mouth

Smash Mouth’s “All Star” became one of the most popular songs from 1999.

It’s a song that’s all about staying hopeful and not giving up.

With its catchy tune, it was everywhere – in movies, on TV, and at sports events.

18. “Angel” by Sarah McLachlan

Sarah McLachlan’s “Angel” is a hauntingly beautiful ballad that touches the soul with its ethereal melody and poignant lyrics.

Its timeless message of hope and redemption resonates with listeners, earning it a place among the most beloved songs from 1999.

19. “Smooth” by Santana featuring Rob Thomas

Santana’s “Smooth” featuring Rob Thomas is a fusion of Latin rock and pop that took the world by storm.

Its irresistible groove and electrifying guitar riffs made it an instant classic, topping charts for weeks on end.

This song exudes timeless coolness, whether hitting the dance floor or cruising with the windows down.

20. “Unpretty” by TLC

Despite society’s focus on looks, TLC’s “Unpretty” encourages accepting yourself for who you are.

It’s a relatable song that sparked important conversations about self-esteem and body image.

21. “Bills, Bills, Bills” by Destiny’s Child

Destiny’s Child’s song “Bills, Bills, Bills” from 1999 was like a battle cry for taking control of your money.

Its catchy music and strong words made people feel confident and empowered to stand up for themselves.

22. “Save Tonight” by Eagle-Eye Cherry

In Eagle-Eye Cherry’s song “Save Tonight,” he sings about grabbing the chance before it’s gone.

The music is soothing, and the words are deep, making you feel nostalgic and like you need to act fast before it’s too late.

23. “Last Kiss” by Pearl Jam

Pearl Jam’s rendition of “Last Kiss” reimagines a classic love story with haunting sincerity.

Its raw emotion and soulful vocals resonate deeply with audiences, making it one of the unforgettable songs from 1999.

24. “Fortunate” by Maxwell

Maxwell’s song “Fortunate” is a smooth, romantic tune from the late ’90s.

With his silky voice, he sings about feeling grateful and in love.

The music is soothing, and the words make you feel warm inside, enhancing your feelings when you listen.

25. “All I Have to Give” by Backstreet Boys

In “All I Have to Give,” the Backstreet Boys deliver a heartfelt promise of love and devotion.

Their harmonious melodies and sincere lyrics capture the essence of first love, making it a timeless favorite among songs from 1999.

26. “Bailamos” by Enrique Iglesias

Enrique Iglesias’ “Bailamos” ignites the dance floor with infectious Latin rhythms and passionate energy.

Its irresistible beat set the tone for romance and excitement, making it one of the standout songs from 1999.

27. “What’s It Gonna Be?!” by Busta Rhymes featuring Janet

Busta Rhymes and Janet Jackson collaborate seamlessly in “What’s It Gonna Be?!” delivering a dynamic blend of hip-hop and R&B.

Its pulsating beats and sensual vocals captivate listeners and ignite confidence and passion.

28. “What It’s Like” by Everlast

Everlast’s introspective narrative in “What It’s Like” explores life’s complexities.

Its poignant storytelling and soulful delivery prompt reflection and empathy, profoundly impacting listeners.

29. “Fly Away” by Lenny Kravitz

Lenny Kravitz takes listeners on a sonic journey of liberation with “Fly Away.”

Its infectious groove and uplifting lyrics serve as an anthem for freedom and adventure, making it one of the standout songs from 1999.

30. “Someday” by Sugar Ray

With “Someday,” Sugar Ray delivers a breezy, feel-good anthem that embodies the carefree spirit of the late ’90s.

Its catchy melody and laid-back vibe make it perfect for lazy days in the sun, earning it a spot among the top songs from 1999.

31. “Lately” by Divine

Divine’s soulful rendition of “Lately” captivates listeners with its heartfelt emotion and smooth vocals.

Its timeless appeal makes it a cherished ballad of 1999, perfect for romantic evenings or moments of introspection.

32. “That Don’t Impress Me Much” by Shania Twain

Shania Twain’s sassy attitude shines in “That Don’t Impress Me Much.”

Its catchy hooks and playful lyrics capture the essence of independence and confidence, making it a standout among songs from 1999 that resonates with listeners of all ages.

33. “Wild Wild West” by Will Smith featuring Dru Hill and Kool Moe Dee

Will Smith’s infectious energy fuels “Wild Wild West,” a funky hip-hop anthem that pays homage to the classic Western genre.

Its catchy beats and playful lyrics transport listeners to a world of adventure and excitement, making it one of the memorable songs from 1999.

34. “Scar Tissue” by Red Hot Chili Peppers

“Scar Tissue” by Red Hot Chili Peppers is a touching song about life’s struggles and how we deal with them.

The line “with the birds I share this lonely view” reminds us of when we feel alone but find solace in nature or shared experiences. 

35. “Heartbreaker” by Mariah Carey featuring Jay-Z

Mariah Carey and Jay-Z join forces in “Heartbreaker,” delivering a sizzling R&B hit that oozes with charisma and style.

Its infectious rhythm and captivating vocals dominated the songs from 1999, cementing its status as a must-listen track of the era.

36. “I Still Believe” by Mariah Carey

“I Still Believe” by Mariah Carey is one of the heartfelt songs from 1999 that effortlessly showcases Carey’s powerful vocals and emotional depth, making it a timeless favorite among fans of her music.

37. “The Hardest Thing” by 98 Degrees

“The Hardest Thing” by 98 Degrees is a heartbreaking song about the difficulty of ending a relationship when you still have lingering feelings for someone.

The lyrics convey the struggle of a man torn between his ex-girlfriend, who wants to reconcile, and his current partner, who trusts him completely

38. “Summer Girls” by LFO

“Summer Girls” by LFO is a catchy 1999 summer anthem with quirky lyrics referencing Abercrombie & Fitch, Larry Bird, and Macaulay Culkin.

It reached No. 3 on the Billboard Hot 100 and was certified platinum by the RIAA.

Billboard ranked it the 14th-biggest summer song of all time in 2010.

39. “Can I Get A…” by Jay-Z featuring Amil and Ja Rule

“Can I Get A…” is a song by Jay-Z featuring Ja Rule and Amil.

It was on the Rush Hour soundtrack and Jay-Z’s third album, Vol. 2… Hard Knock Life.

40. “Jumper” by Third Eye Blind

“Jumper” by Third Eye Blind blends an upbeat tune with heartfelt lyrics tackling the serious theme of a friend considering suicide.

The opening line, “I wish you would step back from that ledge, my friend,” expresses care and concern.

41. “Doo Wop (That Thing)” by Lauryn Hill

“Doo Wop (That Thing)” by Lauryn Hill warns against exploitation in relationships, urging respect and self-worth over materialism and promiscuity.

It topped the US Billboard Hot 100 charts, marking Hill as the first female rapper to achieve this milestone.

42. “Mambo No. 5” by Lou Bega

“Mambo No. 5” by Lou Bega is a lively Latin pop and dance-pop hit from 1999 that was popular across Europe, the UK, North America, and Oceania.

It samples a 1949 instrumental mambo and jazz dance song by Cuban musician Dámaso Pérez Prado.

43. “Sweet Lady” by Tyrese

“Sweet Lady” by Tyrese is a smooth R&B track that captures the essence of romance with its sultry vocals and catchy melody.

Released in 1999, it remains a timeless favorite for fans of ’90s R&B jams.

44. “It’s Not Right but It’s Okay” by Whitney Houston

“It’s Not Right but It’s Okay” is a popular song by Whitney Houston from her album “My Love Is Your Love.”

The song addresses infidelity and features powerful vocals by Houston, conveying a message of independence and resilience.

It’s one of the standout R&B songs of 1999.

45. “(God Must Have Spent) A Little More Time on You” by NSYNC

“(God Must Have Spent) A Little More Time on You” by *NSYNC is a touching song that praises someone special.

The lyrics suggest that this person is so extraordinary that it feels as though God put extra care and attention into their creation.

46. “Lullaby” by Shawn Mullins

“Lullaby” by Shawn Mullins is a song about the shallow life in Los Angeles, especially Hollywood.

It tells the story of a rich but unhappy girl who doesn’t understand the world she’s in.

Mullins got the idea from meeting a woman after a gig in LA.

47. “Anywhere” by 112 featuring Lil Zane

Certainly! “Anywhere” by 112 featuring Lil’ Zane is a sultry R&B track from their album, Room 112.

The song invites listeners to explore passion and intimacy in various locations, with Lil’ Zane adding his signature flair. 

48. “Tell Me It’s Real” by K-Ci & JoJo

“Tell Me It’s Real” by K-Ci & JoJo, released in 1999, is a touching R&B ballad that asks lovers to validate their emotions’ sincerity.

The soulful singing and heartfelt lyrics from the duo make this song a timeless treasure from the late ’90s.

49. “Back 2 Good” by Matchbox 20

“Back 2 Good” by Matchbox 20 is about a rocky relationship on the brink of collapse.

It talks about the singer feeling sorry and wanting to make things right.

Written by Rob Thomas and Matt Serletic, the song highlights the idea of repeating the same mistakes.

It’s a standout track from their debut album, “Yourself or Someone Like You.”

50. “808” by Blaque

“808” by Blaque is a sultry R&B slow jam co-written by Natina Reed and R. Kelly.

With its references to 808 drum machines, the song crafts a pulsating bass-driven groove that propelled it to become the group’s first top-10 hit in the United States.

51. “She’s So High” by Tal Bachman

“She’s So High” by Tal Bachman is a popular power pop song released in 1999.

It portrays a man’s admiration for a seemingly perfect woman.

It reached number 14 on the US Billboard 100 and won a Juno Award for Best Producer.

52. “She’s All I Ever Had” by Ricky Martin

“She’s All I Ever Had” by Ricky Martin is a heartfelt love song expressing deep appreciation and reliance on a significant other.

The lyrics convey vulnerability and emotional dependency, starting with the protagonist feeling broken and alone, with unfulfilled dreams and quiet thoughts

53. “Miami” by Will Smith

“Miami” by Will Smith celebrates the vibrant city of Miami, conveying its lively nightlife, party scene, and diverse culture.

The lyrics express the excitement and energy of the city, likening everyday life to a Mardi Gras celebration

54. “Hands” Jewel

“Hands” by American singer Jewel is a piano-driven ballad from her album Spirit.

Inspired by her personal struggles, including kidney troubles and job loss, Jewel wrote the song after considering stealing a sundress but ultimately decided against it.

The lyrics underscore how small choices can lead to significant change.

55. “Who Dat” by JT Money featuring Solé

“Who Dat” by JT Money featuring Solé is one of those rap songs from 1999 that emphasizes loyalty and credibility within a community, warning against fake friends and imposters.

It peaked at number 5 on the Billboard Hot 100 and is JT Money’s sole solo hit.

56. “Please Remember Me” by Tim McGraw

“Please Remember Me” by Tim McGraw is a touching song about longing to be remembered by a loved one even after parting ways.

It captures the bittersweet essence of lost connections and the enduring power of memories.

57. “From This Moment On” by Shania Twain

“From This Moment On” by Shania Twain is a heartfelt country pop song from her album “Come On Over.”

It highlights Twain’s strong vocals and emotional depth in expressing love.

The song achieved commercial success, reaching high positions on charts worldwide

58. “Love Like This” by Faith Evans

“Love Like This” by Faith Evans is a lively, retro-infused tune that samples Chic’s “Chic Cheer.”

It became one of Evans’s most successful songs, reaching the top forty in New Zealand and the United Kingdom, and peaking at number seven on the US Billboard Hot 100.

The song’s upbeat vibe is infectious.

59. “You” by Jesse Powell

“You” by American R&B singer Jesse Powell is a heartfelt song about love.

Powell talks about how much he loves his partner, describing how she walks, talks, and comforts him.

He wants to be with her forever.

60. “Trippin'” by Total featuring Missy Elliott

“Trippin'” by Total featuring Missy Elliott was a big electro-R&B hit in the late 90s.

It reached number seven on the U.S. Billboard Hot 100 and three on the Hot R&B/Hip-Hop Songs chart.

The remix included DMX and sampled LL Cool J’s “4, 3, 2, 1.”

Furthermore, the music video, directed by Joseph Kahn, added to its memorable vibe.

61. “If You” by Silk

“If You” by Silk is a seductive and romantic song expressing a longing for a deep connection with someone.

Its lyrics delve into desires for physical intimacy and emotional closeness, making it a memorable addition to the songs from 1999.

62. “Ex-Factor” by Lauryn Hill

“Ex-Factor” by Lauryn Hill is a heartfelt song exploring the ups and downs of relationships.

It touches on themes of unreciprocated love and the pursuit of independence.

The track has inspired many artists with its soulful vibe and emotional depth, leading to various covers and samples over the years.

63. “Give It to You” by Jordan Knight

“Give It to You” is Jordan Knight’s first solo single from the self-titled album, which was released in 1999.

It was Knight’s sole top-10 solo hit on the Billboard Hot 100, reaching number 10.

With its infectious electro-funk sound and memorable chorus, the song stood out as a highlight of its time.

64. “Black Balloon” by Goo Goo Dolls

“Black Balloon” by the Goo Goo Dolls is a rock song addressing the challenges of a woman fighting heroin addiction, with her partner striving to help.

Its emotional lyrics and vivid imagery capture the complexities of love and vulnerability.

65. “Spend My Life with You” by Eric Benét featuring Tamia

“Spend My Life with You” by Eric Benét featuring Tamia is a beautiful love song from the album “A Day in the Life” (1999).

It’s about sticking together and loving each other forever.

People who like heartfelt music really enjoy it because it feels special and timeless.

66. “These Are the Times” by Dru Hill

Have you heard ‘These Are The Times’ by Dru Hill? It’s from their album ‘Enter the Dru.’

You know, it hit number 21 on the Hot 100 and snagged the 5th spot on the R&B chart – pretty impressive, right?

The song has this smooth R&B vibe that makes you want to chill out and appreciate the little moments.

67. “I Don’t Want to Miss a Thing” by Mark Chesnutt

“I Don’t Want to Miss a Thing” by Mark Chesnutt is a touching ballad that hits you in the feels.

Came out in ’99, but it still connects with people today.

It’s one of those songs that brings back memories of a time when music really meant something to us.

68. “I Do (Cherish You)” by 98 Degrees

“I Do (Cherish You)” is a romantic song originally written by Keith Stegall and Dan Hill.

In July 1999, vocal group 98 Degrees covered the song, peaking at number 13 on the Billboard Hot 100.

Known for its tender lyrics, the song has become a popular choice for weddings and romantic occasions.

69. “Because of You” by 98 Degrees

“Because of You” by 98 Degrees delves into introspection, exploring a troubled relationship that ended poorly.

With its introspective lyrics, it reached number three on the US Billboard Hot 100 in 1999, making a lasting impact in the musical landscape of the time.

70. “I Will Remember You” by Sarah McLachlan

“I Will Remember You” by Sarah McLachlan is a touching song celebrating cherished moments with a loved one, capturing the beauty of shared memories.

Originally featured in the 1995 movie The Brothers McMullen, McLachlan’s live version in 1999 won her a Grammy Award for Best Female Pop Vocal Performance.

71. “Chanté’s Got a Man” by Chanté Moore

“Chanté’s Got a Man” by Chanté Moore, released in 1999, is a soulful R&B hit that marked Moore’s first top-10 single on the US Billboard Hot 100, reaching number 10.

The song cleverly incorporates an interpolation of the 1971 Osmonds song “One Bad Apple,” adding a nostalgic flair to its success.

72. “Happily Ever After” by Case

“Happily Ever After” is a hit single by American R&B singer Case from his album “Personal Conversation.”

It peaked at number 3 on the Billboard R&B chart and number 15 on the Hot 100 chart, remaining for 20 weeks.

The music video stars a young Beyoncé from Destiny’s Child as his love interest.

73. “My Love Is Your Love” by Whitney Houston

“My Love Is Your Love” by Whitney Houston, released in 1999, was a global hit from her 1998 album of the same name.

It peaked at number four on the US Billboard Hot 100 and sold over 1.4 million copies in the US alone, becoming one of the top-selling singles of 1999.

The album sold over 10 million copies worldwide and achieved quadruple Platinum status in the US.

74. “All Night Long” by Faith Evans featuring Puff Daddy

“All Night Long” by Faith Evans featuring Puff Daddy is a smooth R&B track.

The song samples Unlimited Touch’s “I Hear Music in the Streets” and reached number 9 on the US Billboard Hot 100, solidifying its success among the songs from 1999.

75. “Back That Thang Up” by Juvenile featuring Mannie Fresh and Lil Wayne

“Back That Thang Up” by Juvenile, featuring Mannie Fresh and Lil Wayne, released in 1999, was a major hit from Juvenile’s album “400 Degreez.”

The song had edited versions for radio play and its music video was widely popular in the late 1990s and early 2000s.

76. “Almost Doesn’t Count” by Brandy

“Almost Doesn’t Count” by Brandy Norwood is a poignant ballad about the realization that nearly having a meaningful relationship falls short.

It reached the US Billboard Hot 100’s top 20 and earned Brandy a Grammy nomination for Best Female R&B Vocal Performance.

77. “Man! I Feel Like a Woman!” by Shania Twain

“Man! I Feel Like a Woman!” by Shania Twain celebrates womanhood and empowerment, urging women to embrace joy, freedom, and living without restraint.

78. “Steal My Sunshine” by Len

“Steal My Sunshine” by Len is a popular indie-pop track from their album “You Can’t Stop the Bum Rush” (1999).

Featured on the soundtrack of the film “Go,” it became a summer anthem known for its carefree vibes.

79. “I Need to Know” by Marc Anthony

“I Need to Know” by Marc Anthony is a 1999 blend of R&B and Latin music.

The Spanish version, “Dímelo,” won the Latin Grammy Award for Song of the Year.

Commercially, it charted in the top five in Canada and the United States, marking Anthony’s crossover success into the English-speaking market.

80. “So Anxious” by Ginuwine

Ginuwine’s “So Anxious” from his album 100% Ginuwine captures the thrill of eagerly awaiting a lover’s call and a romantic meet-up.

81. “Faded Pictures” by Case featuring Joe

“Faded Pictures” is a popular R&B duet by Case and Joe, known for its appearance in the movie “Rush Hour” and on Case’s album Personal Conversation.

It peaked at No. 3 on the R&B charts and No. 10 on the Hot 100, becoming a favorite among R&B fans in the late ’90s.

82. “Back at One” by Brian McKnight

“Back at One” by Brian McKnight delves into the essence of love and commitment, portraying the journey of falling in love and nurturing a lasting bond.

The song reached the top ten in various countries, including the United States where it held the number two spot for eight weeks.

83. “When a Woman’s Fed Up” by R. Kelly

“When a Woman’s Fed Up” peaked at number 22 on the Billboard Hot 100 and number 5 on the Hot R&B/Hip-Hop Singles chart.

The music video, directed by Kelly, stars his protégée Sparkle.

Its success added to the notable songs from 1999.

84. “How Forever Feels” by Kenny Chesney

Ever heard ‘How Forever Feels’ by Kenny Chesney?

It’s this catchy tune all about wanting a long-term commitment.

Chesney sings about adventures but admits he hasn’t felt ‘forever’ yet. It’s like he’s searching for that special something.”

85. “Amazed” by Lonestar

“Amazed” by Lonestar, released in March 1999, is a popular country ballad that topped the Billboard country chart for eight weeks.

Its touching lyrics and catchy melody have made it a favorite for weddings and romantic occasions.

A pop remix of the song also reached number one on the Billboard Hot 100 in 2000, enhancing its success.

86. “Sometimes” by Britney Spears

“Sometimes” by Britney Spears is a bubblegum pop ballad from her first album.

It hints at a shy girl’s struggles expressing love.

The song was a hit worldwide, reaching the top ten in many countries and hitting number one in Belgium (Flanders), Netherlands, and New Zealand, while reaching second place in Australia.

87. “Ghetto Cowboy” by Mo Thugs

“Ghetto Cowboy” by Mo Thugs, from their 1998 album Chapter II: Family Reunion, features Layzie Bone, Krayzie Bone, Powder P, Thug Queen, and Layzie Bone’s wife Felecia.

It sampled Kenny Rogers’ “The Gambler”, reaching No. 15 on the Billboard Hot 100 and topping the Hot Rap Singles chart, earning gold certification from the RIAA.

88. “Out of My Head” by Fastball

“Out of My Head” by Fastball is one of the standout songs from 1999.

It is a rock ballad infused with gospel elements, featuring a prominent Hammond organ and piano.

Bassist Tony Scalzo leads as vocalist, with guitarist Miles Zuniga adding harmonies in the final chorus.

89. “Hard Knock Life (Ghetto Anthem)” by Jay-Z

“Hard Knock Life (Ghetto Anthem)” by Jay-Z cleverly samples the chorus from “Annie”, turning it into a gritty reflection on ghetto life.

The song went platinum, earned Jay-Z a Grammy nomination, and later led to his involvement in producing the 2014 film adaptation of Annie.

90. “Jamboree” by Naughty by Nature featuring Zhané

“Jamboree” by Naughty by Nature ft. Zhané is a popular hip-hop song from their album “Nineteen Naughty Nine: Nature’s Fury” (1999).

It hit number 10 on the Billboard Hot 100 and topped the Hot Rap Singles chart.

Known for its catchy chorus and lively feel, it’s a timeless party anthem.

91. “Take Me There” by Blackstreet featuring Mýa, Mase, and Blinky Blink

“Take Me There” was the theme song for “The Rugrats Movie,” reaching No. 1 in New Zealand and attaining platinum status.

In the US, it peaked at No. 14 on the Billboard Hot 100 and No. 21 in Canada.

Released on November 30, 1998, it served as the lead single from the movie’s soundtrack and was featured on Blackstreet’s album, “Finally.”

92. “Stay the Same” by Joey McIntyre

This song promotes self-acceptance and staying true to oneself.

It encourages listeners to embrace their individuality and resist societal pressures.

The song reached No. 10 on the Billboard Hot 100 and was certified gold by the RIAA, marking it as McIntyre’s most successful single.

93. “A Lesson in Leavin'” by Jo Dee Messina

“A Lesson in Leavin'” is a country song first recorded by Dottie West in 1979.

Jo Dee Messina covered it in 1999, reaching No. 2 on the Billboard Hot Country Singles & Tracks chart for seven weeks.

The song portrays a woman’s frustration and hopes that her departing lover will learn from his actions in his next relationship.

94. “Iris” by Goo Goo Dolls

This love song taps into the universal desire for acceptance and meaningful connection.

Created for the 1998 film “City of Angels,” it became one of the band’s most popular songs from 1999, surpassing its initial movie association.

95. “Satisfy You” by Puff Daddy featuring R. Kelly

“Satisfy You” is a popular R&B song from Puff Daddy’s album “Forever” (1999).

The lyrics convey devotion and protection, promising to keep a loved one safe and happy.

It gained popularity and remains a memorable collaboration in the late ’90s music scene

96. “Better Days (And the Bottom Drops Out)” by Citizen King

“Better Days (And the Bottom Drops Out)” by Citizen King, released in 1999, was their breakout single.

Its catchy tune landed its spots in the film “Gone in 60 Seconds” and the TV show “Malcolm in the Middle.”

Despite its success, the band didn’t produce another hit, earning them the label of a one-hit wonder.

97. “Music of My Heart” by NSYNC and Gloria Estefan

“Music of My Heart” is a hit collaboration between Gloria Estefan and NSYNC.

Released in 1999 for the movie “Music of the Heart,” the song reached number two on the Billboard Hot 100 and earned Gold certification in the US.

It won the Billboard Music Award for Top Song from a Movie and was nominated for an Academy Award for Best Original Song.

98. “Write This Down” by George Strait

“Write This Down” is a heartfelt ballad expressing regret from a man who belatedly realizes he has taken his lover for granted.

99. “When You Believe” by Whitney Houston and Mariah Carey

“When You Believe” is a powerful duet by Whitney Houston and Mariah Carey, featured in the 1998 animated film “The Prince of Egypt.”

It’s a song about hope and resilience, reaching #15 on the Billboard Hot 100 charts.

Its success led to it being the lead single for both Whitney’s album My Love Is Your Love and Mariah’s compilation album #1s.

100. “(God Must Have Spent) A Little More Time on You” by Alabama and NSYNC

“(God Must Have Spent) A Little More Time on You” is a song by NSYNC from their debut album.

It’s a heartfelt ballad celebrating love, suggesting divine care.

Alabama also recorded a version blending country with pop.

101. “All the Small Things” by Blink-182

Written by guitarist and vocalist Tom DeLonge, this song pays homage to his then-girlfriend.

Its straightforward lyrics, memorable chorus, and engaging music video propelled it to No. 6 on the Billboard Hot 100 and No. 2 on the UK Singles Chart, becoming one of the standout songs from 1999.

How Well Do You Remember These 101 Songs from 1999?

As we wrap up our journey through the top 101 songs from 1999, it’s evident that this year was a treasure trove of musical gems.

They weren’t just hits in the moment; they’re timeless bangers.

Whether you were jamming out in your room back then or just discovering them now, you gotta admit, they’re classics.

Got a favorite from ’99 that we missed?

Share it in the comments!

Let’s keep the nostalgia train rolling!

And if you enjoyed this post, check out more awesome song lists we’ve got, like:

• The Top 101 Songs From 1983 (With Spotify Playlist)
• The Top 101 Songs From 1985 (With Spotify Playlist)
• The Top 101 Songs From 1986 (With Spotify Playlist)