Here's what happened after Ashlee Simpson disappeared from the spotlight

In 2004, Ashlee Simpson cast herself as the antithesis of her pop princess sister Jessica Simpson and burst out of the shadow with her own eponymous MTV reality show and the triple-platinum debut album, Autobiography. For teens of the early aughts, she was a refreshing, Converse-clad signal of rebellion peering out behind her choppy bangs — so much so that when she debuted her alleged nose job in 2006, it sparked outrage among Marie Claire readers who were "disappointed" by the star's perceived lack of realness, according to The New York Times. But Ashlee has always been authentic, even whilst somehow recreating Milli Vanilli's mistakes. Following her seeming career-ruining Saturday Night Live performance — which may just be the most disastrous SNL spot in history — the singer came clean about her voice-stealing acid reflux and managed to top the Billboard album charts a year later with her follow up I Am Me. 

Then, her priorities shifted. Ashlee tied the knot with Fall Out Boy bassist Pete Wentz — beginning their rightful reign as emo's arguable king and queen — and had her first child Bronx Mowgli. She released Bittersweet World, her final album for a decade, and retreated from the spotlight to "focus on motherhood," according to The New York Times. Though Simpson has largely shied away from the public eye, she's been coming back for more in recent years.

Ashlee Simpson 'lucked out' co-parenting with Pete Wentz

Ashlee Simpson's marriage to Pete Wentz was the kind of stuff Myspace bulletins were made of. It was a big deal, but alas, much like the social network famed for championing emo's brightest stars, it did not last. According to Entertainment Tonight, the pair thanked each other fr th mmrs and split in 2011, which devastated the rocker.

In a 2015 interview with Howard Stern on his Sirius XM radio show (via E! News), Wentz admitted that he believed their marriage would last forever, but it suffered when he hit a wall following his band's 2010 hiatus. "It was the first time where I was like, 'Well, no one's really taking my picture. I'm just basically hanging out with my kid all day. Who cares?' I think when you stop caring about your personal appearance, your personal hygiene, it makes you even more depressed," he said, "but it makes you do it more. It's like a vicious cycle."

Though Wentz was initially angry that Simpson "bailed on [him]" in his lowest moment, they ultimately worked out their divorce without the expensive lawyers they initially hired. By 2018, Simpson revealed to Us Weekly that she feels like she's "lucked out" with Wentz co-parenting Bronx. Even her second husband, Evan Ross, admitted they're "all really close friends."

Ashlee Simpson met her second husband in the club

Remember Ryan Cabrera? Yes, that spiky-haired guy that wooed Ashlee Simpson with his acoustic guitar throughout The Ashlee Simpson Show. His music video for "On The Way Down" is basically a time capsule of the era. The Hills fans last saw the singer-songwriter when he briefly resurfaced on New Beginnings to date Audrina Patridge, rebooting his career as an MTV reality show boyfriend, but he also happens to be the common link between Ashlee Simpson and her second husband, Evan Ross.

Simpson and Ross, the son of legendary Supremes singer Diana Ross, had been running in the same social circles for a long time. According to The New York Times, the actor happened to be "good friends" with Cabrera (at least before he broke bro-code) and met Simpson at a friend's birthday party in a Hollywood club. On their E! series Ashlee + Evan, Ross explained that Simpson initially tried to impress with a dance-off. "You were lifting your leg up and stuff, trying to show me that you dance better than me, I think," Ross said. "I was like, 'Oh my goodness. What's happening right now?'"

The pair hit it off immediately, and the night ended in a steamy makeout where they — in Ross' words — "dry humped a little bit. "That was the best dry humping I've ever done in my life 'cause I put my best work in," he said. TMI, you two crazy kids.

A whirlwind romance

Sometimes, when you know, you know — and Evan Ross knew almost immediately that Ashlee Simpson was the one. It was mere weeks after their first initial dry hump, but The Hunger Games: Mockingjay star didn't stop in the name of love and drop down on one knee until a little bit later. The actor told E! News, "I was giving it time only because I wanted to give it time, but I would have asked her a month after I was with her."

To be fair, the pair didn't actually wait that long to tie the knot. Ross popped the question in 2014 after about six months of dating and shared the news the way any old fashioned Hollywood whirlwind romance should — on social media. In a tweet, the actor revealed a blissfully glowy photo showcasing Simpson's unconventional engagement ring. According to People, the five-carat, ruby-and-diamond stunner was based on a vintage setting, and Ross worked closely to design the ring with celebrity jeweler Neil Lane under the obviously tight deadline.

Once Simpson said yes, her future mother-in-law Diana Ross stepped in to help plan the wedding. Evan told E! News that she's "involved in all levels of my life. She's one of the most incredible mothers ever."

She tied the knot in Diana Ross' backyard

About seven months after Ashlee Simpson said yes to Evan Ross, she walked down the aisle in a stunning backyard wedding. It was immediately clear that Diana Ross had taken her wedding planning duties to an entirely new level.

According to Us Weekly, the 200-guest event took place at the Supremes singer's Greenwich, Connecticut estate, which was decorated with dream catchers and other eclectic bohemian accents. Though the mother of the groom is historically known to hang back — shelling out for the rehearsal dinner and never outshining the mother of the bride — Diana officiated the ceremony and performed her 1981 hit "Endless Love" at the reception. Not everyone's mom is Diana Ross. It just comes with the territory. Evan's half-sister Tracee Ellis Ross was also involved and served as the receptions (likely hilarious) MC.

As far as the Simpson family goes, Bronx walked the singer down the aisle. Jessica Simpson was the matron of honor, and her two children — Maxwell and Ace — took on flower girl and ring bearer duties. The bridesmaids all wore shoes from Jessica's line, while Ashlee stunned in a long-sleeved wedding dress, a tiara, and $750,000 worth of diamonds and rubies from Neil Lane (the same guy who made her engagement ring).

"The wedding went perfectly," Diana gushed to Us Weekly. "We had a beautiful rainbow surrounding us, loving family and friends ... dancing the night away."

Ashlee Simpson's delivery room had some uninvited guests

Not long after Ashlee Simpson tied the knot for a second time, she revealed that she was expecting her another child — her first with Evan Ross. Their daughter, Jagger Snow, was born on July 30, 2015, and that day, the maternity ward was bustling a bit more than usual in no small part due to Diana Ross.

In an interview with People, Simpson and Evan revealed that the most memorable part of their daughter's birth wasn't the birth itself (Ashlee had already been there, done that). It was when their parents busted in the delivery room before they got the okay. There ain't no mountain high enough to keep a grandmother like Diana away from the birth of her grandchild.

"While [Ashlee] was having the baby, we said we were going to do it just us, but then we saw both our parents behind the curtain watching," Evan told the magazine, adding, "Also, those nurses can't stop my mom! Like, Diana Ross just walks in." Casual, huh?

She tried her luck on reality TV a second time

Ashlee Simpson has led a relatively private life while taking a nearly eight-year-long hiatus from her TV career to raise her children. In 2018, she made the difficult choice to jump back into the spotlight with Evan Ross. In an interview with Rolling Stone, Ashlee admitted that she was doing her E! series Ashlee + Evan (which documented the making of the pair's duet album), a little differently than the typical semi-scripted reality series. There are no roses to give away here. Instead, it was meant to be "as close to a documentary as possible," a sort of throwback to the era of Behind the Music.

Ross isn't a stranger to the small screen, either, with roles in series like Star and Wicked City. Still, Simpson claims the pair are "very private." She had to prep her hubby for the highs and lows of reality TV.  "I was like, 'OK, babe, we have to open our hearts and just do this because if you do it, you have to be there and open yourself and open the door,'" she told Rolling Stone.

Ross didn't seem that concerned. In an episode of Watch What Happens Live, the actor revealed that he didn't think it would affect their marriage. "I don't think it's possible to ruin a relationship because of anything you do. I think it has to do with whether or not you're supposed to be together," he said.

Ashlee + Evan lasted six episodes

As it turned out, Ashlee + Evan didn't have the same success as The Ashley Simpson Show, but that may have been a personal choice. The Melrose Place actress, who originally told Rolling Stone that her kids inspired her to do the series, ended up pulling out — at least in part — because of said kids. Simpson told Us Weekly, "[We] didn't want to have our kids on TV for too long," and after the short run of six episodes, the pair had moved on from their duets album and were focusing on separate endeavors.

"We are not doing that anymore," Simpson told the magazine. "We had so much fun doing it, but we're both working on our own projects and we're literally there with each other every day."

That didn't stop the tabloids from speculating that there were troubles in the singer's marriage. RadarOnline claimed the pair got into a "huge fight" because Ross allegedly didn't want to do the show and thought it made them "look like failures." Considering the couple's general lovey-dovey nature — and the fact they couldn't help but covertly smooch during a guest appearance in a 2020 episode of The Bachelor: Listen to Your Heart – we're guessing it's fine.

Diana Ross pushed Ashlee Simpson to sing again

After a decade-long hiatus — and millions of records sold — Ashlee Simpson finally relaunched her music career. This time, the star teamed up with Evan Ross for an EP of duets called Ashlee + Evan. This album was a long time coming. The Autobiography singer told Spotify that in the early days of her relationship with Ross, they'd say up "until 3:00 in the morning singing together," but this was just something they did for fun. They never dreamed of working together until Simpson stopped by the studio while Ross was making his own album, and they recorded the song "Permission To Love." The flood gates were open, but the timing was wrong — Simpson was about to be raising a newborn.

Diana Ross was the one who pushed for the album to happen. Evan told Rolling Stone that his mom had wanted them to do it "for a while" because she "loves the way [they] sound together." She even lent her talents to one of the tracks, writing the melody for "Whole Lot of Love." Still, she wasn't the one who gave them a concrete deadline to finally pull the trigger; it was their reality show. " ... It put a time limit on things," Evan told Spotify. "Otherwise we'd probably be making music forever. Though I'm sure we'll still be making music together forever."

Ashlee Simpson took her whole family on tour

Ashlee Simpson and Evan Ross are living out their Partridge Family dream. In 2018, the pair revealed to Us Weekly that they were trying to make touring "a family thing." Think: that Winnebago vacation you took with your dad to the Grand Canyon, except you're living on a luxury tour bus, your parents are signing autographs, and no one is inexplicably using a paper map suggesting that the GPS is telling lies. Hey, it's probably not that strange for Ross considering touring is practically a part of his family's DNA.

These touring dreams finally became a reality when the Simpson-Ross family set out to support their joint album. It turns out, being with family on the road is actually the best part of the whole experience. "It could be a lonely process taking you far away from your family," Ross told Forbes about touring. "In this circumstance, we were able to be with our family and children and have a good time. Every day we got to feel like we were still at home because home is where the heart is."

It wasn't just fun for mom and dad. Simpson told Forbes that the kids "loved" the tour, and their daughter would even "stay up really late" to sing the last song of their set — as if that kid isn't going to be a star!

She launched a clothing collection with Evan Ross

Ashlee Simpson isn't just living in the shadow of Jessica Simpson's music career. Though the Autobiography singer didn't launch her own $1 billion retail empire like her older sister, she did wade in the shallow end of the fashion industry with a 2018 unisex capsule collection for Zadig & Voltaire.

Like Ashlee's reality show and duets album, the line — named Jagger Snow after her daughter — was a joint effort with her husband. The pair notoriously share clothes, so it made sense to make something they could both wear. In an interview with the Los Angeles Times, Ashlee admitted when she first started dating Ross, it was like "Yes, a new wardrobe!" Ross, who likes to wear Ashlee's kimonos and vintage tees, agreed. "We got together and got a whole new closet," he told the newspaper.

The pair's collection features a cashmere sweatshirt, denim trucker jacket, a tee-shirt, and boyfriend jeans (or girlfriend jeans depending on who is borrowing what from whom). Ross did the drawings featured on the clothes, pulling inspiration from the pair's own lyrics and the late Michael Jackson's wardrobe in his "They Don't Care About Us" music video — who also happened to be a family friend to Diana Ross

Baby number three for Ashlee

Ashlee Simpson and Evan Ross are having a hard time figuring out how big their family should be. Ross, who has 10 siblings, told Entertainment Tonight that he wanted five more. Simpson apparently just wanted one more but was taking it "one at a time." Perhaps, she'll change her mind in the future.

Though we don't know what number the pair will ultimately end up on, Simpson is putting in the work. In early May 2020, the star revealed she was expecting her third child — her second with Evan Ross — in an Instagram post. "We are so excited to share it with everyone," she captioned a picture of the couple holding a Clear Blue pregnancy test. 

Two weeks later, the singer cut into an adorable blue gender reveal cake to let fans know they were having a baby boy. "Haha Jagger had us laughing," Simpson wrote in the comments section (captured by Page Six). "She thought for sure it was a baby sister but she's excited now!"

Ashlee Simpson's rock star lifestyle is shockingly low key

Ashlee Simpson is used to partying with rock stars — if not because she is one, then because of her relationships. She spent the early aughts riding with Fall Out Boy and Ryan Cabrera. Her mother-in-law is Diana Ross. Her sister is Jessica Simpson. Her ex-brother-in-law sang in 98 Degrees. Okay, so none of these people are as notoriously raucous as, say, The Rolling Stones or Black Sabbath, but we didn't expect the singer's married life to be as truly tame as it is.

In Ashlee + Evan (as recapped by RadarOnline), we saw the couple argue about Evan's partying ways. He wanted to hang with his friends, Ashlee wanted to rest up for work. Truthfully, the singer has become the kind of wholesome star that suits her past on 7th Heaven. The pair aren't hanging around the Met Gala or jet-setting to Glastonbury. Instead, they're supporting Febreze — yes, the cleaning product — which released an album called The Freshness for some unintelligible reason. According to Forbes, fans asked for it. We don't know who these fans are, but Ashlee and Evan went to the launch party. "Music doesn't have to be so serious," Ross told Forbes in his iron-clad defense. A thrilling date night, indeed. Maybe there were free drinks.