Ashlee Simpson has a slew of iconic hits under her belt, including Pieces of Me, Boyfriend, Outta My Head, Invisible, and more which establishes the singer's stellar status in the industry. But despite her illustrious career and strong footing, Simpson has attracted substantial negative media throughout her life, hindering her from rising to her potential fame. Being the younger sister of the overtly successful Jessica Simpson didn't work best for her either. Despite being put against her elder sister, and consistently being subjected to her shadow, the Simpson sisters remain supportive of each other.
Born on October 3, 1984, in Waco, Texas, Ashlee kicked off her showbiz journey after Jessica's early success with her debut album, Sweet Kisses. Ashlee toured with her sister as a backup dancer while working as a jobbing actress. She would garner wide recognition through Jesicca and her several acting credits before eventually proving her vocal talents with the release of her debut album, Autobiography, as a 19-year-old. She has since released two more successful albums and raked stellar credits in films and television.
Inside Ashlee Simpson's First Married Life!
The Boyfriend crooner has been married twice; in fact, she was in her early 20s and at the onset of her promising career when she decided to delve into marriage and parenthood. Ashlee met the Fall Out Boy bassist Pete Wentz at the 2006 VMAs and started dating him shortly. "I've always liked guys that have an inner geek. I'm an inner geek myself," Simpson said as she made her romance with Wentz official in 2006. The pair tied the knot within two years of dating in May 2008 and welcomed their firstborn, Bronx, after a few months.
Rumors of a bumpy marriage started surfacing within a year of their nuptials, and although the pair vehemently contradicted the swirling speculation, things started falling into place after Simpson filed for divorce in 2011. "We remain friends and deeply committed and loving parents to our son," the pair's statement read. "I didn't [anticipate the split]. At the same time, we were both very young," Wentz said years after their divorce.
The Fall Out Boy bassist shares how he thought their marriage was meant to be a "forever thing." Reflecting on his long-dissolved marriage with the singer, Wentz revealed their relationship unraveled after his band went on a hiatus in 2010. "I would be an idiot to think that I didn’t contribute to the unraveling of it," he said. The estranged couple remains amicable to this day. Wentz, 43, has since gone on to father two children with his long-time partner, Meagan Camper.
The singer-turned-actress's dating slate wasn't neat before Wentz. Ashlee had dived into the celebrity dating pool pretty early, starting with actor Josh Henderson, with whom she was linked during the onset of her career. The Pieces of Me crooner went on to have a brief rapport with Carson Daly, Gregory Smith, and Nick Carter, who reportedly cheated on Paris Hilton with Simpson.
Ashlee Simpson's Second Marriage with Evan Ross!
Simpson bounced back fast after her divorce from Pete. She moved on with actor Vincent Piazza and enjoyed a year-long dating bliss with him. But little did she know that her to-be second husband was already there in her life for a long time. Ashlee and actor Evan Ross have been friends for over ten years, but it was only in 2013 that the pair took their relationship up a notch. Ross called Simpson "the one" early in their dating scene and got down on his knees after a year in 2014.
The lovebirds wasted no time in starting their happy ever after and got hitched at the Diana Ross' Greenwich, Connecticut, estate in August 2014. The singer and actor couple welcomed their first kid, daughter Jagger, in July 2015, followed by the birth of son Ziggy in 2020. It's more than eight years as spouses and the pair is still going strong. Ashlee and Evan's happy and pretty normal conjugal life was showcased in the short-lived reality series, Ashlee + Evan, on E! in 2018.
"The biggest thing in this world is in love. I'm so in love. I love my daughter, I love my wife. She's given me the best gift in the world. I'm very lucky," said Ross, who rarely misses a chance to gush about his wife and their amazing kids. Evan is best known as the son of the Grammy-winning entertainer Diana Ross. Evan is an actor and musician himself. Some of his notable credits are Pride, According to Greta, Supremacy, and The Hunger Games: Mockingjay – Part 1.
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