In 1999, Pamela Anderson appeared as a giantess in the music video for "Miserable" by California alternative rock band Lit.
Her role as C.J. Parker gave her more popularity and gained her attention from international viewers. She returned to Baywatch for the 2003 reunion movie, Baywatch: Hawaiian Wedding. Pamela Anderson also appeared on The Nanny as Fran's rival, Heather Biblow.

In 2006, Jessica Simpson then returned to the recording studio, switching labels from Columbia to Epic Records. On 29 August 2006, Jessica Simpson released her fourth album A Public Affair, the album debuted at #5 on the Billboard 200, with 101,000 copies sold in its first week, and spent 10 weeks on the Billboard.

Matt Damon's attempts at essaying leading characters in romantic dramas such as 2000's All the Pretty Horses and The Legend of Bagger Vance were commercially and critically unsuccessful. Variety said of his work in All the Pretty Horses: "[Damon] just doesn't quite seem like a young man who's spent his life amidst the dust and dung of a Texas cattle ranch. Nor does he strike any sparks with [Penelope] Cruz." Matt Damon was similarly deemed "uncomfortable being the center" of Robert Redford's The Legend of Bagger Vance.

Brooke Burke and Hough danced a Foxtrot the following week, receiving the first 30 from the judges, plus a group Paso Doble with Maurice Greene and Warren Sapp. The group received a 29 which was added to Burke's score giving her a 59/60 plus the encore for that week. The following week, she danced a Tango and Mambo which she would have to do a 15-second solo. Brooke Burke received a 28 for her first dance and a 27 for the second dance. The following week, she danced a Jive and received a 21, her lowest score and for the first time came in last place for her first dance. Her second dance was a Salsa which received a 28 and tied with Warren Sapp for second place. The following week, she danced a group Samba and received a 28 for her solo. Her second dance was Freestyle which received a 30 from all judges. Her final dance was a repeat of her Viennese Waltz which received a 30. Brooke Burke later won the season and the mirror ball trophy beating Warren Sapp and Kym Johnson.

After Taylor Swift returned to Pennsylvania, she was asked to sing at the U.S. Open tennis tournament, where her rendition of the national anthem received much attention. Swift started writing songs and playing 12-string guitar when she was 12. Taylor Swift began to regularly visit Nashville and wrote songs with local songwriters. By the time she was 14, her family decided to move to an outlying Nashville suburb.

When Alessandra Ambrosio was 12 years old, she enrolled in modeling classes, then began modeling for Dilson Stein at age 15. Winning Brazil's Elite Model Look started her modeling career in earnest. Her first notable modeling job was the cover of Brazilian Elle magazine. Elite passed along some of her Polaroids to Guess which led her booking the Millennium GUESS? campaign along with friend and fellow Brazilian Ana Beatriz Barros. Alessandra Ambrosio has since worked with brands including Revlon, Christian Dior, Giorgio Armani, Rolex, Oscar de la Renta, Gucci, Escada, Rocco Barocco, Calvin Klein and Ralph Lauren, as well as the Pirelli Calendar.

Megan Fox has spoken extensively of her time in education; that in middle school she was bullied and picked on and she ate lunch in the bathroom to avoid being "pelted with ketchup packets". Megan Fox said that the problem was not her looks, but that she had "always gotten along better with boys" and that "rubbed some people the wrong way". Megan Fox also said of high school that she was never popular and that "everyone hated me, and I was a total outcast, my friends were always guys, I have a very aggressive personality, and girls didn’t like me for that. I’ve had only one great girlfriend my whole life".In the same interview, Megan Fox mentions that she hated school and has never been "a big believer in formal education" and that "the education I was getting seemed irrelevant. So, I was sort of checked out on that part of it".

Bret Michaels released a 30-minute DVD from (Time Life) in 2008 called Hard & Heavy Confidential featuring Bret Michaels which included acoustic versions of "All I Ever Needed", "Driven", "Every Rose Has Its Thorn" and "Something to Believe In", it also included in depth interviews. The DVD was included in the Hard & Heavy cd/dvd collection from (Time Life) advertised on TV by Bret Michaels. The same 4 acoustic performances were also released on CD which was titled "Bret Michaels Acoustic Sessions."