"Wifey" is a song by American R&B trio Next. The song was written by Eddie Berkeley, Keir Gist, band member Robert "RL" Huggar, and singer Lil' Mo for the group's second studio album, Welcome II Nextasy (2000). The song was released as the album's lead single on May 8, 2000. "Wifey" peaked at number one on the US Billboard Hot R&B/Hip-Hop Singles & Tracks chart while reaching number seven on the Billboard Hot 100. It also entered the top 20 in New Zealand and the United Kingdom. In 2001, the song won an AWARD Rhythm & Soul Award for in the Award-Winning R&B/Hip-Hop Songs category.
"Angel" is a song by Canadian singer-songwriter Sarah McLachlan. The song first appeared on McLachlan's fourth studio album, Surfacing, in 1997 and was released as the album's fourth and final single in September 1998. The lyrics are about the death of musician Jonathan Melvoin (1961–1996) from a heroin overdose, as McLachlan explained on VH1 Storytellers. It is sometimes mistitled as "In the Arms of an Angel". or "Arms of the Angel".
"Summer Girls" is a song by American pop group LFO. It was released on June 29, 1999, as the lead single from their debut album, LFO (1999). "Summer Girls" reached number three on the US Billboard Hot 100 chart was certified platinum by the Recording Industry Association of America (RIAA). In 2010, Billboard magazine named it the 14th-biggest summer song of all time. In 2019, Billboard also ranked the song the 43rd-greatest song of 1999. This was the band's first single to feature Devin Lima as a member of the group after original member Brian "Brizz" Gillis left the group.
"Bailamos" is a single by Spanish singer Enrique Iglesias sung in Spanglish. The song was released in 1999 as part of the soundtrack to the film Wild Wild West (1999) and later included on Iglesias's fourth and debut English-language album, Enrique (1999). "Bailamos" reached number one on the Spanish Singles Chart and on the US Billboard Hot 100, and it became a top-three hit in Canada, Hungary, New Zealand, Norway, and Sweden. In both New Zealand and Spain, it was the second-most-successful single of 1999.
"Hunter" is a song by British singer Dido from her debut album, No Angel (1999). The song was released as the third single from the album in the United States on 18 June 2001. "Hunter" reached number 17 on the UK Singles Chart and peaked within the top 50 in Australia, France, Greece, Ireland, and New Zealand. In the US, it entered the top 20 on two Billboard charts.
"Maria Maria" is a song by American rock band Santana featuring the Product G&B, included on Santana's 18th studio album, Supernatural (1999). The song was written by Wyclef Jean, Jerry "Wonda" Duplessis, Carlos Santana, Karl Perazzo, and Raul Rekow, while Jean and Duplessis produced it. The track samples the drum beat from "God Make Me Funky" by American jazz fusion band the Headhunters, and the melody riff was inspired by the Wu-Tang Clan song "Wu-Tang Clan Ain't Nuthing ta Fuck Wit". Interspersed with guitars and other strings, "Maria Maria" is driven by a hip hop beat. At the 2000 Grammy Awards, the song won Best Pop Performance by a Duo or Group with Vocals before it experienced commercial success.
"Bent" is a song by American alternative rock band Matchbox Twenty. The rock ballad was shipped to radio on April 17, 2000, as the lead single from their second album, Mad Season, and was given a commercial release in the United States on July 5, 2000. "Bent" became the band's first and only song to top the US Billboard Hot 100, reaching number one on the chart dated July 22, 2000, and spending one week at the position. The song also topped the RPM 100 Hit Tracks chart in Canada for five nonconsecutive weeks. "Bent" was nominated for Best Rock Song at the 43rd Annual Grammy Awards and won the award for Most Performed Foreign Work at the APRA Music Awards of 2001.
"The First Night" is a song by American singer Monica for her second studio album, The Boy Is Mine (1998). It was written by Tamara Savage and Jermaine Dupri, featuring production and additional vocals from the latter. Built around a sample of Diana Ross's 1976 recording "Love Hangover", penned by Marilyn McLeod and Pam Sawyer, who share co-writing credits, the song is about the protagonist's battle with sexual temptations on the night of her first date, despite her conflicting emotions and strong sexual desires.
"He Wasn't Man Enough" is a song by American R&B singer and songwriter Toni Braxton. It was written by Rodney "Darkchild" Jerkins, Fred Jerkins III, LaShawn Daniels, and Harvey Mason, Jr. for her third studio album, The Heat (2000), while production was helmed by the former. "He Wasn't Man Enough" is an uptempo R&B song that differs from Braxton's previous ballads. The song was released by LaFace Records on February 29, 2000, as the lead single from the album.
"Most Girls" is a song by American singer Pink, released as the second single from her debut album, Can't Take Me Home (2000). It was released on June 6, 2000, and, after spending 16 weeks on the US Billboard Hot 100 chart, peaked at number four on November 25. The song also reached number one in Australia, where it was certified platinum, number two in Canada and New Zealand, and number five in the United Kingdom.
"Dear Lie" is a song by American group TLC. It was written by Kenneth "Babyface" Edmonds and band member Tionne "T-Boz" Watkins for the trio's third studio album FanMail (1999), featuring production by Edmonds. The song was released as the album's third and final single on December 6, 1999, peaking at number 51 on the US Billboard Hot 100 and reaching the top 40 in several other countries. "Dear Lie" is included on the group's 2009 compilation album, We Love TLC.
"My Love Is Your Love" is a song by American singer Whitney Houston. It was written and produced by Wyclef Jean and Jerry Duplessis for Houston’s fourth studio album of the same name (1998). Released on May 31, 1999, as the album's fourth single, it received positive reviews and was successful worldwide, hitting the top 10 in 23 international markets. The song peaked at number four on the US Billboard Hot 100, number two in the United Kingdom, and number one in New Zealand. It was later certified platinum by the Recording Industry Association of America (RIAA).
"Heartbreak Hotel" is a song by American singer Whitney Houston. Originally written for inclusion on TLC's third studio album FanMail, it was later recorded by Houston after TLC rejected the song. The song was written by Carsten Schack, Kenneth Karlin and Tamara Savage, and produced by Soulshock & Karlin. It was released on December 15, 1998, by Arista Records, as the second single from Houston's 1998 album My Love Is Your Love. The song prominently features R&B singers Faith Evans and Kelly Price during the choruses and bridge.
"Nobody's Supposed to Be Here" is a song by Canadian recording artist Deborah Cox, released as the lead single from her second studio album, One Wish (1998). Written by Montell Jordan and its producer, Anthony "Shep" Crawford, the song was released on the same day as the album, on September 15, 1998, by Arista Records. It is Cox's most successful song, peaking at number two on the Billboard Hot 100 for eight weeks and spending a then-record 14 weeks at number one on the Hot R&B Singles & Tracks chart. In 2017, Billboard ranked the song at number five on its "Greatest of All Time Hot R&B/Hip-Hop Songs" chart.
"Unpretty" is a song by American group TLC, released on May 17, 1999, through LaFace and Arista Records as the second single from the band's third studio album, FanMail. It was written by Tionne "T-Boz" Watkins and the producer Dallas Austin. Austin assisted Watkins in adapting the latter's written poem into "Unpretty" after feeling disgusted by an episode of American talk show Ricki Lake.
"You're Makin' Me High" is the lead single from American singer Toni Braxton's second studio album, Secrets (1996). The mid-tempo song represents a joint collaboration between the Grammy Award-winning producer Babyface and Bryce Wilson. The beat of the song was originally for singer-songwriter Brandy, with Dallas Austin pegged to write a lyric to override; however, Braxton had Babyface write lyrics for the song. It was ultimately issued in the United States as a double A-side with "Let It Flow", the airplay hit from the 1995 film Waiting to Exhale.
"Put Your Lights On" is a song by American rock band Santana and American musician Everlast from Santana's 18th studio album, Supernatural (1999). Serviced to US rock radio in August 1999, the song peaked at number 18 on the Billboard Bubbling Under Hot 100 and number eight on the Billboard Mainstream Rock Tracks chart. "Put Your Lights On" won a Grammy Award for Best Rock Performance by a Duo or Group with Vocal at the 42nd Annual Grammy Awards.
"Swear It Again" is a song by Irish boy band Westlife. The ballad was released on 19 April 1999 in the United Kingdom as the first single from their debut album, Westlife (1999). The song peaked at number one on the UK Singles Chart for two weeks, giving Westlife their first of 14 UK number-one singles. "Swear It Again" is Westlife's only single to have charted in the US, peaking at number 20 on the Billboard Hot 100 and ranking number 75 on the Billboard Hot 100 year-end chart in 2000.
"The Game of Love" is a song by American rock band Santana from their 19th studio album, Shaman (2002). The vocal performance on the song is by Michelle Branch. It was composed by Gregg Alexander and Rick Nowels. The song was released as a single on September 23, 2002, and won a Grammy Award for Best Pop Collaboration with Vocals. Commercially, "The Game of Love" peaked at number five on the US Billboard Hot 100 chart and topped the Billboard Adult Contemporary chart, becoming that ranking's most successful track of 2003. The song also reached the top 10 in Canada, New Zealand, and six European countries.
"Nobody Knows" is a song by R&B singer Tony Rich from his 1996 debut album, Words. Released as his debut single on November 7, 1995, the song peaked at number two on both the Billboard Hot 100 and Billboard Hot Adult Contemporary Tracks charts. It also became a hit in several other countries, topping the Irish Singles Chart and reaching number two in Australia and Canada, number four in the United Kingdom, and the top 20 in the Netherlands, New Zealand, and Sweden. Rich received a nomination for the 1997 Grammy Award for Best Male Pop Vocal Performance.
