Life in Pics
Photo flashback: Jessica Simpson's life and career in pictures
By Jessica Wedemeyer 11:18am PDT, Jul 8, 2020
Jessica Simpson closes out her fourth decade on July 10, 2020. In honor of her 40th birthday, Wonderwall.com is taking a look back at her biggest moments caught on camera. Keep reading to relive the highlights from her time in the spotlight — from headline-making moments in her love life to the major achievements in her career, family milestones and more…
RELATED: Stars turning 40 in 2020
Jessica Simpson's love life was noteworthy before she even released her first single. In 1998, she posed with then-boyfriend Jensen Ackles at the launch party for Teen People magazine at Planet Hollywood in Los Angeles. Years later, the singer-actress alleged that the "Supernatural" star cheated on her with LeAnn Rimes.
RELATED: Forgotten celeb couples of the '90s
Jessica Simpson was all smiles while performing at Madison Square Garden in New York City on Oct. 28, 1999. Her very first studio album, "Sweet Kisses," debuted the following month, on Nov. 23, 1999.
RELATED: Female singers of the '90s: Where are they now?
Jessica Simpson reportedly met Nick Lachey at the Hollywood Christmas Parade in 1998. The following year — on Dec. 8, 1999 — they made their red carpet debut as a couple at the Billboard Music Awards in Las Vegas. It wasn't just their personal lives that were entwined: She toured with his band, 98 Degrees, and served as an opening act on their "Heat It Up" tour in 2000.
Jessica Simpson and then-boyfriend Nick Lachey went in for a kiss while posing with their surfboard trophies for "choice love song" for their duet "Where You Are" during the Teen Choice Awards in Santa Monica, California, on Aug. 6, 2000.
Jessica Simpson's parents — mom Tina Simpson and dad Joe Simpson, a Baptist youth minister who also served as her manager — joined her at a party for her sophomore album, "Irresistible," on June 4, 2001.
Nick Lachey asked Jessica Simpson to be his wife on a yacht off the coast of Hawaii in February 2002. A few months later — on July 10, 2002 — she showed off her massive engagement ring as they sat together at the ESPY Awards in Hollywood.
Jessica Simpson posed alongside Ashton Kutcher in a promotional photo for her acting debut: She had a three-episode stint as Kelso's girlfriend Annette — a blonde version of Mila Kunis's Jackie — on the fifth season of "That '70s Show" in 2002 and 2003.
Jessica Simpson and Nick Lachey tied the knot at a church in Austin, Texas, on Oct. 26, 2002. At her first red carpet event as a married woman — the premiere of "The Hot Chick" in Los Angeles on Dec. 2, 2002 — the singer-actress made sure photographers got a clear shot of her brand new diamond-encrusted wedding band stacked alongside her massive engagement ring.
Jessica Simpson also posed with little sister Ashlee Simpson, who made her feature film debut in "The Hot Chick," at the premiere of the comedy in Los Angeles on Dec. 2, 2002.
Jessica Simpson and her new husband, Nick Lachey, posed on the beach to promote their MTV reality show, "Newlyweds: Nick & Jessica," which debuted on Aug. 19, 2003. The series ran for three seasons until March 30, 2005, and launched the couple to a new level of superstardom.
Jessica Simpson posed with a copy of her third album, "In This Skin," at the Virgin Megastore in New York City's Times Square on the day it debuted: Aug. 19, 2003. Her fourth studio album, "ReJoyce: The Christmas Album," debuted the following year, on Nov. 23, 2004.
Jessica Simpson gave husband Nick Lachey the look of love as they posed with their award for favorite reality show for "Newlyweds" during the People's Choice Awards in Pasadena, California, on Jan. 9, 2005. The previous year, they won a Teen Choice Award for the show.
Jessica Simpson met John Mayer — and posed for a photo with him — at the annual pre-Grammy Gala and Salute to Industry Icons in Beverly Hills on Feb. 12, 2005. The duo exchanged contact information, started writing each other letters and then began dating the following year after her marriage to Nick Lachey came to an end.
Jessica Simpson debuted her eponymous clothing line at the MAGIC fashion trade show in Las Vegas on Feb. 15, 2005. The brand has since become (easily) the most lucrative endeavor of her career. It's expanded to include accessories, footwear, swimwear and jeanswear as well as tween, girls and maternity collections.
Jessica Simpson rocked Daisy Dukes' signature short shorts in a promotional photo for the 2005 big screen adaptation of "The Dukes of Hazzard" — her feature film debut. She earned two MTV Movie Award nominations for her efforts in the action comedy, which failed to impress critics but opened at No. 1 at the box office.
Jessica Simpson sat beside co-star Johnny Knoxville before a special screening of "The Dukes of Hazzard" at the Marine Corps Air Station Miramar in San Diego on July 29, 2005. At the time, there were rumors that the duo were having an affair, which thy both denied. Nearly 15 years later, in her memoir "Open Book," the singer-actress finally admitted that she and the "Jackass" star had an emotional affair while she was still married to Nick Lachey.
On Nov. 17, 2005, Jessica Simpson and Nick Lachey posed together at a Gucci presentation in Beverly Hills. Less than a week later, on Nov. 23, they released a joint statement announcing that they were going their separate ways. In the final years of their marriage, they were plagued by rumors of infidelity. Between 2004 and 2005, there were reports that Jessica cheated with Johnny Knoxville, Adam Levine, Fred Durst and Bam Margera, who maintained in 2006 that they hooked up after a night of margaritas.
On Jan. 10, 2006, Jessica Simpson took home the People's Choice Award for favorite song from a movie for her cover of "These Boots Are Made For Walkin'" from the "Dukes of Hazzard" soundtrack. She also won a Teen Choice Award for best female breakout performance in a film for her work in the action comedy.
Jessica Simpson autographed a copy of her fifth studio album, "A Public Affair," outside the "Total Request Live" studios in New York City on Aug. 29, 2006 — just three days after it debuted.
Jessica Simpson returned to the big screen opposite Dane Cook in 2006's "Employee of the Month." (Around the time they co-starred in the rom-com, there were rumors that the pair were also getting friendly off set.) Jessica scored a Teen Choice Award nomination for best actress in a comedic film for her performance in the funny flick. She went on to star in 2007's "Blonde Ambition" and in the 2009 straight-to-DVD comedy "Private Valentine: Blonde & Dangerous." She also portrayed versions of herself in 2008's "The Love Guru" and on a 2010 episode of "Entourage" before leaving acting behind.
Jessica Simpson famously dyed her hair brown in early 2007 as her romance with John Mayer started heating up. She debuted her new look at the Sony and BMG Grammy Awards party in Los Angeles on Feb. 11, 2007.
Jessica Simpson and then-boyfriend John Mayer attended the Met Gala together in New York City on May 7, 2007. Their toxic off-and-on romance finally came to an end later that year.
Jessica Simpson started seeing Tony Romo in late 2007. The singer-actress was snapped sharing a tender moment with the NFL star as they watched the Dallas Mavericks take on the Los Angeles Lakers at the American Airlines Center in Dallas, Texas, on March 18, 2008.
Jessica Simpson performed on "Good Morning America" at ABC's studios in New York City's Times Square on Sept. 9, 2008 — the same day her sixth studio album, "Do You Know," debuted. Following the release of her first effort at country-pop, she released just one more album, 2010's "Happy Christmas, before leaving music behind.
Jessica Simpson and then-boyfriend Tony Romo made their final public appearance as a couple at the National Golf Tournament in Bethesda, Maryland, on July 1, 2009. Just eight days later — the night before her 29th birthday — he broke up with her. In her 2020 memoir "Open Book," Jessica alleged that the football star dumped her after accusing her of cheating on him with ex-boyfriend John Mayer. (She maintains she was faithful to the quarterback.)
Jessica Simpson made her big return to reality TV with "The Price of Beauty." The short-lived VH1 show chronicled the singer-actress, BFF CaCee Cobb and hairstylist Ken Pavés as they traveled the globe exploring how different cultures view the concept of beauty. On Oct. 8, 2009, the trio were snapped shooting in Morocco. The series debuted five months later but came to an end after just eight episodes on May 3, 2010.
On Dec. 4, 2009, Jessica Simpson was snapped leaving a New York City hotel with Billy Corgan, prompting rumors they were dating. The following year, the Smashing Pumpkins frontman claimed they were collaborating on the theme song for her reality show "The Price of Beauty," though he stopped short of insisting things between them were strictly platonic.
Jessica Simpson was snapped sharing a laugh with Patricia Arquette and rumored fling Jeremy Renner at Vanity Fair's afterparty following the White House Correspondents' Association Dinner in Washington, D.C., on May 1, 2010. At the time, there were rumors that the singer-actress was hooking up with the Oscar-nominated actor.
Jessica Simpson started seeing Eric Johnson in mid-2010. They made their official debut at the launch party for the Show Me Your Blues collection from her eponymous clothing line in New York City on Sept. 7, 2010. Two months later, a rep for the singer-actress confirmed that she and the former professional football player were engaged. They tied the knot on July 5, 2014.
On Nov. 29, 2011 — a month after Jessica Simpson confirmed rumors that she and then-fiancé Eric Johnson were expecting their first child together — her baby bump made its red carpet debut at the Footwear News Achievement Awards in New York City. Their daughter, Maxwell Drew, arrived the following year.
Jessica Simpson chatted with a contestant on the first season of the NBC reality show "Fashion Star," which debuted on March 13, 2012. She served as a mentor on both seasons of the series, which concluded in May 2013.
Jessica Simpson welcomed her first child, daughter Maxwell Drew Johnson, on May 1, 2012. Later that year, she made headlines after scoring a deal with Weight Watchers worth a reported $4 million to chronicle her post-baby slimdown. The following year — on March 23, 2013 — Maxi made her official debut posing with her mama and aunt Ashlee Simpson at an event for Jessica's eponymous maternity collection in Charlotte, North Carolina. At the time, the singer-actress was pregnant with her second child, son Ace Knute Johnson.
Family of four! Jessica Simpson's second child with then-fiancé Eric Johnson, son Ace Knute, arrived on June 30, 2013. He made his big debut at an event for her eponymous clothing collection at a Dillard's in Dallas, Texas, on Nov. 23, 2013. Big sis Maxwell Drew was also on hand!
It was a double date for two pairs of newlyweds when Jessica Simpson and husband Eric Johnson joined her little sister, Ashlee Simpson, and her new husband, Evan Ross, at a party following the premiere of "The Hunger Games: Mockingjay – Part 1" — in which Evan appeared — in Los Angeles on Nov. 17, 2014. (Jessica and Eric wed in July 2014, while Ashlee and Evan tied the knot in August 2014.)
Jessica Simpson posed with her parents — dad Joe Simpson and mom Tina Simpson, who'd divorced two years earlier — at a party celebrating the 10th anniversary of her eponymous clothing line in New York City on Sept. 9, 2015.
Jessica Simpson and husband Eric Johnson welcomed their third child, daughter Birdie Mae, on March 19, 2019. The mother of three made headlines when she stepped out in New York City on Sept. 25, 2019, and debuted her slim post-baby body, signaling the beginning of a major transformation for the singer-actress.
Girls night out! Jessica Simpson was snapped pushing her bundled-up baby girl, third child Birdie Mae Johnson, in a stroller during a New Year's Eve outing with family members including her older daughter, Maxwell Drew Johnson, and mom Tina Simpson, in Aspen, Colorado, on Dec. 31, 2019.
Jessica Simpson posed with a copy of her memoir, "Open Book," at a Barnes & Noble in New York City on Feb. 4, 2020. The book — which made headlines and then topped the New York Times Best Sellers list — debuted two days earlier.
Jessica Simpson made it a family affair at a celebration for her memoir, "Open Book," at Stella 34 Trattoria at Macy's in New York City on Feb. 5, 2020. She posed with husband Eric Johnson and their three kids: daughters Birdie Mae and Maxwell Drew and son Ace Knute. The singer-actress and her hubby celebrated their sixth wedding anniversary on July 5, 2020.
Theo Kingma/Shutterstock
Globe Photos/Mediapunch/Shutterstock
Canova/Mediapunch/Shutterstock
Chris Weeks / Getty Images
Jim Spellman / WireImage
Kevin Mazur / WireImage
Fox/Photofest
Jon Kopaloff / Getty Images
Gregg DeGuire / WireImage
Bob Riha Jr. / WireImage
James Devaney / WireImage
Danny Moloshok/EPA/Shutterstock
Erik Jensen / Getty Images
Warner Bros/Kobal/Shutterstock
London Entertainment/Shutterstock
Fairchild Archive/Penske Media/Shutterstock
Michael Germana/Shutterstock
Nancy Rivera/Shutterstock
Lionsgate/Kobal/Shutterstock
Picture Perfect/Shutterstock
Matt Baron/BEI/Shutterstock
Ron Jenkins/Fort Worth Star-Telegram/Tribune News Service / Getty Images
Al Pereira / WireImage
Ron Sachs/Shutterstock
GI/AJ / WireImage
Dimitrios Kambouris/VF1 / WireImage
Jamie McCarthy / WireImage for Jessica Simpson Collection
Tyler Golden / NBCU Photo Bank/NBCUniversal via Getty Images
Jamie McCarthy / Getty Images for Jessica Simpson Collection
Frazer Harrison / Getty Images
Kristina Bumphrey/Starpix/Shutterstock
Raymond Hall / GC Images
NEMO/ NGRE / BACKGRID
Kristin Callahan/ACE Pictures/Shutterstock
Kevin Mazur / Getty Images for Macy's
Up Next Disney darlings now