1999
April
- Jessica Simpson could be heard on the TV show Dawson Creek soundtrack with "Did You Ever Love Somebody."
October
- Jessica Simpson hit the Top 40 for the first time with "I Wanna Love You Forever."
- Jessica Simpson opened for several Ricky Martin concert dates.
November
- Jessica Simpson released her debut LP, Sweet Kisses. CDNow said of Jessica and her new LP: "...Her vocals are the typical Top 40 combination of breathy wonder mixed with moments of chest-thumping sincerity, but Simpson at least seems to mean it more than, say, Britney Spears, who never seems to mean anything."
- The single "I Wanna Love You Forever" was certified gold.
October
- Sweet Kisses was certified gold.
- The single "I Wanna Love You Forever" was certified platinum.
- Jessica Simpson hit the Top 10 with "I Wanna Love You Forever."
- "I Wanna Love You Forever" topped the Billboard Hot 100 Singles Sales chart for 6 weeks.
2000
January
- Jessica Simpson hit #1 for 2 weeks with "I Wanna Love You Forever."
March
- Jessica Simpson's second single "Where You Are" (a duet with boyfriend Nick Lachey of 98 Degrees) hit the charts and was featured in the film Here On Earth.
April
- Jessica Simpson and Nick hit the Top 10 with "Where You Are"
June
- Jessica Simpson hit the Top 40 with "I Think I'm In Love With You."
- Sweet Kisses was certified platinum.
August
- Jessica Simpson hit #1 in Canada with with "I Think I'm In Love With You."
- Jessica Simpson won 2 Teen Choice Awards for Breakout Artist and Love Song of the Year ("Where You Are").
November
- Sweet Kisses was certified 2x platinum.
2001
January
- Jessica Simpson was nominated for an American Music Award for Favorite Pop/Rock New Artist.
April
- Jessica Simpson was nominated for a Blockbuster Entertainment Award for Favorite Female - New Artist
May
- Jessica Simpson hit the Top 40 with "Irresistible."
June
- Jessica Simpson released her 2nd LP, Irresistible.
- Jessica Simpson hit the Top 10 with "Irresistible."
July
- Irresistible was certified gold.
October
- Jessica Simpson hit the Top 40 with "A Little Bit."
2002
July
- This Is The Remix was released.
September
- Jessica Simpson appeared in 1 episode of That '70s Show on FOX.
October
- Jessica Simpson married Nick Lachey of 98 Degrees.
2003
January
- Jessica Simpson was back guest-starring in a few episodes of That '70s Show on FOX.
August
- Jessica Simpson hit the Top 40 with "Sweetest Sin."
- Jessica Simpson released her next LP, In This Skin.
- Jessica Simpson is on MTV with the reality series Newlyweds: Nick And Jessica.
November
- Jessica Simpson signed a comedy development deal with ABC.
- Jessica Simpson appeared on the cover of Rolling Stone with the caption 'Housewife of the Year.'
- Jessica Simpson hit the Top 40 with "With You."
December
- In This Skin was certified gold.
2004
January
- Jessica Simpson hit the Top 10 with "With You."
- Jessica Simpson co-hosted Saturday Night Live with her husband, Nick Lachey.
- The second season of Newlyweds began on MTV.
February
- In This Skin was certified platinum.
- Jessica Simpson hit #1 for 2 weeks with "With You."
March
- Jessica Simpson released a revamped version of In This Skin with 2 new songs - the covers of Robbie Williams' "Angels" and Berlin's "Take My Breath Away."
- Jessica Simpson topped the Billboard Mainstream Top 40 chart with "With You."
- Jessica Simpson hit the Top 40 with "Take My Breath Away."
April
- Jessica Simpson and Nick Lachey appeared in their first TV variety special on ABC with The Nick & Jessica's Variety Hour.
- In This Skin was certified 2x platinum.
- Jessica Simpson hit the Top 10 with "Take My Breath Away."
- Jessica Simpson was featured on VH1's Divas Live.
May
- A TV sitcom starring Jessica Simpson was not picked up for the fall schedule.
June
- Jessica Simpson hit the Top 40 with "Angels."
- Jessica Simpson had to cancel some concert performances due to a kidney infection.
August
- The video for "With You" was nominated for 2 MTV Video Music Awards including Best Female Video and Best Pop Video. Jessica performed at the ceremony held in Miami.
October
- The single "With You" was certified gold.
November
- Jessica Simpson was nominated for 2 American Music Awards for Favorite Pop/Rock Female Artist and Favorite Pop/Rock Album. Jessica also performed at the ceremony.
- Jessica Simpson recorded a duet ("Little Drummer Boy") with her sister Ashlee Simpson for Jessica's holiday LP, Re-Joyce: The Christmas Album.
- Jessica Simpson appeared with her hubby in their ABC Christmas special, Nick And Jessica's Family Christmas.
December
- In This Skin was certified 3x platinum.
2005
January
- Re-Joyce: The Christmas Album was certified gold.
July
- Jessica Simpson could be heard on the soundtrack for The Dukes Of Hazzard with her cover of "These Boots Were Made For Walking."
- Jessica Simpson topped the Billboard Hot Digital Tracks chart with "These Boots Were Made For Walkin'."
- Jessica Simpson's video for "These Boots Were Made For Walkin'" irked a Christian group that called for it to be cleaned up.
August
- Jessica Simpson could be seen in her first feature film - The Dukes Of Hazzard. The movie opened to poor reviews but over 30 million opening weekend bucks.
November
- The singles "With You" and "These Boots Were Made For Walkin'" were certified platinum, and "Take My Breath Away" was certified gold.
December
- Jessica Simpson filed for a divorce from Nick Lachey.
2006
March
- Jessica Simpson switches record label (Columbia Records) to Epic Records.
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