Bittersweet World was released on April 22^nd, 2008, and is Ashlee Simpson’s third studio album and currently the last. She has not released a new album since. Bittersweet World did not do as well as her prior two albums. She was not able to have a hit single from the album. The lead single Outta My Head (Ay Ya Ya) was not able to chart on the Billboard Hot 100 and was widely ignored by radio. Nevertheless, Bittersweet World is turning 15.

Bittersweet World went in a different direction sonically compared to her previous two albums. Bittersweet World has gotten comparisons to Gwen Stefani’s music which I can see some resemblance. This would have been two years after Gwen Stefani’s album Sweet Escape. I think Bittersweet World is a fun pop album. I think it is underrated. Ashlee Simpson does not have that many iconic songs in her catalogue partly since she does not have that many albums. Her iconic songs are Pieces of Me, La La, and Shadow from her debut album Autobiography and Boyfriend and L.O.V.E. from sophomore album I Am Me. Pieces of Me was a huge hit on the Billboard Hot 100 and on radio. By the time Bittersweet World came out, it was after Ashlee Simpson’s Lip-Synching Saturday Night Live scandal. That could explain to some degree why the album did not do so well. It seemed a lot of the public had moved on from Ashlee Simpson. 2008 was also the year that we would get new pop stars in Katy Perry and Lady Gaga. Also pop was shifting to more dance music which was Lady Gaga’s signature sound on her debut album.

Bittersweet World got overshadowed. It was also released at the same time as Madonna’s album Hard Candy which had the hit single 4 Minutes which featured Justin Timberlake and Timbaland. Timbaland served as a producer of Bittersweet World. Some may call Bittersweet World a guilty pleasure. I don’t think of it as a guilty pleasure because there is nothing to feel guilty about. It’s an album that is fun and has fun and catchy songs. The lead single Outta My Head (Ay Ya Ya) is fun. Rule Breaker has similarities to some of Kesha’s style of music. This also came out before Kesha would enter the music scene. Bittersweet World is for the most part an up tempo album. It only has one or two ballads. Never Dream Alone is a slow song. Little Miss Obsessive has a lighters up type of vibe. A lot of the songs on the album are songs I can picture in movies and television. I am not sure if any of these songs have been featured in either medium. I know other songs have been, including Pieces of Me and La La. Ashlee Simpson’s music has been featured in Smallville and had a famous scene where Anette O’Toole, who was Martha Kent, sang along to La La in the kitchen. She was possessed by a high school girl. Smallville was the origin story of the teenager Clark Kent, who would become Superman.

If Bittersweet World had been a few years later or today, would it have found better success? It’s possible. I’m not sure. Even if it came out now, I am not sure if it would do well unless it was made by Olivia Rodrigo or Taylor Swift. Ashlee Simpson has never been the biggest pop star and has not been the most liked. A lot of the public has mixed reactions to Ashlee Simpson as well as her sister Jessica Simpson who was famous first. Currently neither are active in music. Ashlee Simpson always seemed to be overshadowed by Jessica Simpson and seemed known as the younger sister. Even though Ashlee Simpson does not have that many hits, she has had better success with longevity for the few hits she does have compared to her sister. Both of Ashlee Simpson’s prior albums hit number 1 on the Billboard chart. I think it is time for Ashlee Simpson to make a comeback. If she were to release new music, I am curious how the reception would be this time around. I think Ashlee Simpson has been overshadowed when compared to other artists. I think there is room for Ashlee Simpson to have a music comeback. Hopefully one day in the near future there will be a fourth album. What is exciting the most is the growth and evolution that would come with a new album given how long it’s been since the last one.