1999

April

- Jessica could be heard on the TV show Dawson Creek soundtrack with “Did You Ever Love Somebody.”

October

- Jessica hit the Top 40 for the first time with “I Wanna Love You Forever.”
- Jessica opened for several Ricky Martin concert dates.

November

- Jessica 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 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 hit #1 for 2 weeks with “I Wanna Love You Forever.”

March
- Jessica’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 and Nick hit the Top 10 with “Where You Are”

June

- Jessica hit the Top 40 with “I Think I’m In Love With You.”
- Sweet Kisses was certified platinum.

August

- Jessica hit #1 in Canada with with “I Think I’m In Love With You.”
- Jessica 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 was nominated for an American Music Award for Favorite Pop/Rock New Artist.

April

- Jessica was nominated for a Blockbuster Entertainment Award for Favorite Female – New Artist

May

- Jessica hit the Top 40 with “Irresistible.”

June

- Jessica released her 2nd LP, Irresistible.
- Jessica hit the Top 10 with “Irresistible.”

July

- Irresistible was certified gold.

October

- Jessica hit the Top 40 with “A Little Bit.”

2002

July

- This Is The Remix was released.

September

- Jessica appeared in 1 episode of That ’70s Show on FOX.

October

- Jessica married Nick Lachey of 98 Degrees.

2003

January

- Jessica was back guest-starring in a few episodes of That ’70s Show on FOX.

August

- Jessica hit the Top 40 with “Sweetest Sin.”
- Jessica released her next LP, In This Skin.
- Jessica is on MTV with the reality series Newlyweds: Nick And Jessica.

November

- Jessica signed a comedy development deal with ABC.
- Jessica appeared on the cover of Rolling Stone with the caption ‘Housewife of the Year.’
- Jessica hit the Top 40 with “With You.”

December

- In This Skin was certified gold.

2004

January

- Jessica hit the Top 10 with “With You.”
- Jessica 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 hit #1 for 2 weeks with “With You.”

March

- Jessica 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 topped the Billboard Mainstream Top 40 chart with “With You.”
- Jessica hit the Top 40 with “Take My Breath Away.”

April

- Jessica 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 hit the Top 10 with “Take My Breath Away.”
- Jessica was featured on VH1′s Divas Live.

May

- A TV sitcom starring Jessica was not picked up for the fall schedule.

June

- Jessica hit the Top 40 with “Angels.”
- Jessica 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 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 recorded a duet (“Little Drummer Boy”) with her sister Ashlee Simpson for Jessica’s holiday LP, Re-Joyce: The Christmas Album.
- Jessica 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 could be heard on the soundtrack for The Dukes Of Hazzard with her cover of “These Boots Were Made For Walking.”
- Jessica topped the Billboard Hot Digital Tracks chart with “These Boots Were Made For Walkin’.”
- Jessica’s video for “These Boots Were Made For Walkin’” irked a Christian group that called for it to be cleaned up.

August

- Jessica 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 filed for a divorce from Nick Lachey.

2006

March

- Jessica switches record label (Columbia Records) to Epic Records.

July

- Jessica hit the Top 40 with “A Public Affair.”

August

- Jessica won a Teen Choice Award for Choice Movie Breakout, Female. Jessica also co-hosted the ceremony.
- Jessica released A Public Affair.

September

- Jessica topped the Billboard Hot Dance Club Play chart with “A Public Affair.”
- A Public Affair was certified gold.

2007

July

- The single “A Public Affair” was certified gold.

December

- Jessica starred in the film Blonde Ambition which didn’t make it at the box-office and released on DVD within 2 months.

2008

June

- Jessica hit the Billboard Country Songs chart with “Come On Over.”

September

- Jessica released her country LP Do You Know
- Jessica topped the Billboard Country Albums chart with Do You Know

Source: RockOnTheNet.com