- Celebs
ByAcacia Deadrick
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The world has watched thestunning transformation of Emily Osment. Before becoming known to children of the '00s as Lilly Truscott, the former child star had roles in projects like "3rd Rock from the Sun,""Touched by an Angel," and even "Friends." Emily, who's the sister of Haley Joel Osment, also played Gerti Giggles in the second and third installments of the "Spy Kids" franchise. In 2006, Emily's life changed forever when she joined the cast of "Hannah Montana," as the series went on to become one of the Disney Channel's most successful original programs of all time and spawned a hit feature film.
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Alot has happened for Emily since "Hannah Montana"ended. While many fans have spent time speculating thetruth about Emily's friendship with former co-star Miley Cyrus, Emily has been focused on other things. She's maintained a career in the entertainment industry, successfully navigating the transition from child star to adult actor, and much of her work has been quite notable. Here's what EmilyOsment has been up to since her Disney days.
She focused on her music career after Hannah Montana ended
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The final episode of "Hannah Montana" aired on January 16, 2011. The stars of the show all went their separate ways career-wise, with Emily Osment turning her focus to music after more than a decade working as a child actor. "I was kind of doing both for as long as I can remember. I love music more than anything else,"Osment told Disney Dreaming of her transition from acting to music."I had been writing and playing music since I was little ... It was about three years ago when I decided I wanted to make this official ... It's been so much fun, I've been able to work with some amazing people."
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The transition wasn't all that sudden for Osment, though. She released some music before "Hannah Montana" officially went off-air, including her 2009 EP "All The Right Wrongs" and her debut studio album "Fight or Flight," which was released in 2010. "Fight or Flight" was met with mostly positive feedback, receiving a 2.5/5 star rating fromAllMusicand 4/5 stars from users on the same site, something seen as an achievement given Osment's career up to that point. "I kind of just did my own thing. I listen to a lot of Alanis Morissette, I kind of got inspired from her and her song 'Jagged Little Pill' ... There's a lot of edge to [the album] ... I love hearing the guitars and the drums in the songs," Osment said of her album.
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Emily Osment went on a couple of concert tours
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Like all former child stars, Emily Osment had to work to shed her Disney persona. After "Hannah Montana" ended, the star was still routinely asked questions about the series. One way Osment broke out of her "Hannah Montana" shell was by focusing on her music. As noted, Osment released some music, and she went on multiple concert tours with her full-length album.
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"As soon as the show wrapped I flew to Canada and headlined the Soda Pop tour for almost two months. I love being on tour and being able to give myself fully to the music and participate in every aspect of the creative process. I plan to continue promoting my record abroad and hope to keep a steady great relationship with my fans," Osment told The Starlight Craze of her life post-Disney Channel.
Osment spent the bulk of two years out on tour, traveling throughout Canada and the United States, and evening making it to Brazil and the Bahamas for some shows. The singer toured with acts like Hot Chelle Rae, Drake Bell, and even her former co-star Mitchel Musso, who played Oliver on their Disney show. But Osment never saw performing as a permanent departure from acting. "I really do love both of the ways that I chose to spend my time and I don't think I could ever choose just one," she said of her two career paths.
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She studied acting at college
Child actors take a variety of different paths when they become adults. While some push through in the industry, others escape for a more typical route. After her brief foray into music, Emily Osment decided to go to college. "I'm going off to college. It'll be nice because I'll have this four-year period to figure out what I want to do next, which is mainly film, when I'm not doing music," Osment said of her plans, as reported by Sweety Highin 2010.
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Before enrolling in classes, though, the former child star took some time to travel. "Berlin, 2011 after I deferred college for a year to read books and ride trains and wear combat boots and scarves across the globe," Osment captioned a throwback photo on Instagram. After her global sojourn, Osment began her freshman year at Occidental College in Los Angeles, California.
Like many child stars, Osment studied theater in college. Unlike most of her classmates, however, she was already a well-known figure among her age group, making her college experience unique. "I went to a little college and I knew everyone there. There were some people who were a little weird ... and things got kinda weird," Osment told Teen Vogue.
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Emily Osment starred in a failed TV show
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While still in college, Emily Osment kept busy with acting projects. The star lent her voice to a variety of films and television series, including "Beverly Hills Chihuahua 2" and "From Up on Poppy Hill." She appeared in an episode of "Two and a Half Men," and she starred in the TV movie "Cyberbully," among other projects.
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One of her most notable, however, was a failed series called "Cleaners." Osment starred alongside Emmanuelle Chriqui as a female assassin in the action show, making what was perhaps the biggest departure from "Hannah Montana" yet. In an interview with PopStop TV, Osment shared that director Paul Leyden piqued her interest in the project. "I've never had so much fun on a project," she said. "It's rare that you find something where the material is great, the cast is great, the crew is great, and you all really like to have a good time together. And that's what this whole experience was."
Unfortunately for Osment, the experience didn't last long. The cast shot a six-episode first season, and the series was picked up for a second, but after another 12 episodes, "Cleaners" was canceled.
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She then starred in the series Young & Hungry
Luckily for Emily Osment, she had another series lined up before "Cleaners" even began. The former Disney star moved to Freeform (then ABC Family) to star in the comedy series "Young & Hungry." Osment played a personal chef to a tech billionaire in the series, which was produced by her former Disney friend Ashley Tisdale.
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"I think this differs a lot from the other shows on TV right now. It pushes the envelope quite a lot. It's realistically sexy and realistically funny,"Osment told Pop City Life in 2014 ahead of the series' debut."It follows the story of a girl who isn't perfect and who doesn't have her life together. I think that's what we see too much of on TV — these perfect characters. This girl's a mess and it's fun to watch. I think that's what really sets us apart."
"Young & Hungry" fared relatively well in the TV world, lasting for five seasons before being canceled. Tisdale, Jesse McCartney, Giada De Laurentiis, and Rachael Ray were among the guest stars to appear throughout its run, and it garnered lots of loyal fans. The ending came as a disappointment to many, though, as Season 5 ended on a cliffhanger. The cast and crew believed they were going to film a sixth season, but the network had other plans.
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She had a couple of long-term relationships
While Emily Osment doesn't divulge every detail of her personal life on social media, she has shared the truth about her dating life. And during the 2010s, the actor had a couple of long-term relationships. In 2013, Osment started dating Jimmy Tatro, an actor known for his work in films like "Diary of a Wimpy Kid: Rodrick Rules" and "Theater Camp," as well as the series "Home Economics." Osment told The Sun of her and Tatro (via Distractify), "We don't publicly talk about [our relationship], but if you follow us on social media, you could figure it out." After the two broke up, Tatro began a relationship with Zoey Deutch.
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Osment moved on, too. After ending things with Tatro, she reportedly began dating a guy named Jim Gilbert who apparently worked in the mental health space. "'I'm not sure if there is a type of therapy for this.' -my therapist boyfriend," Osment wrote on X, formerly known as Twitter, in 2016 at the time she was reportedly dating Gilbert. The actor also briefly dated Nathan Keyes, pictured above, and although those relationships didn't last, Osment did find lasting love after (more on that later).
Emily Osment joined the Hallmark universe
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For some actors, getting the call to join the Marvel Cinematic Universe is a badge of honor — or at least the signal of a giant paycheck. For others, starring in a Hallmark film is just as rewarding. It may not come with the same payout as being a superhero, but it's often an emotionally fulfilling venture. Such was the case when Emily Osment joined the Hallmark universe in 2018 with her starring role in "Christmas Wonderland."
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"I grew up watching Hallmark Christmas movies — anything Christmas. My family loves Christmas movies. There's usually a bunch of reasons you do a movie, but for me the opportunity to get out of town and drive my car to Utah where we shot it, was great. It came at the perfect time so when it landed in my in-box I was like, 'Let's go!'" Osment said to Media Village about her enthusiasm for her first Hallmark film.
Osment's work with Hallmark didn't end there. In 2021, she returned to the network to star as Leah in "A Very Merry Bridesmaid," and Osment worked alongside "Days of Our Lives" alum Casey Deidrick. "When I first read the script, I was really taken by the story of Leah and her journey throughout it, the girl that's surrounded by so many people that are in their own world and forget to celebrate her when she need to be celebrated the most," Osment said of the role in an interview with Hallmark.
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She landed her own Netflix show
If there's anything on par in show business with joining the Marvel Cinematic Universe, it might be landing a starring role in a Netflix series. Emily Osment hit the jackpot in the latter in 2021 when she led "Pretty Smart," a romantic comedy series about an intelligent woman who moves in with her sister after a breakup.
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"After meeting with them, it just seemed like a no-brainer. I've been a friend of Netflix for a long time and they're always so kind to me," Osment said to Decider of deciding to work with creators Jack Dolgen and Doug Mand on the project. "Especially after the year and a half that we've had, to be able to bring joy and comedy back into people's living rooms or bathtubs or wherever you watch TV, I don't care. We want you to be happy, you know?"
Unfortunately Osment's bid to bring happiness to others through "Pretty Smart" didn't last. While audiences generally enjoyed the series, it premiered to poor critical feedback. And apparently not enough viewers streamed the series because it was canceled after just one season. After "Pretty Smart" ended, Osment continued lending her voice to "Family Guy," as she had on occasion beginning in 2012, and she took a voice over role in the series "Dead End: Paranormal Park."
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She joined the cast of a popular sitcom
Emily Osment just might be destined to be a sitcom star. In 2022, Osment returned to the familiar format as a recurring character, Mandy McAllister, in Season 5 of "Young Sheldon," the popular spin-off of the even more popular series "The Big Bang Theory." Ahead of Season 6, it was announced that Osment had been promoted to series regular, and she remained in that role through Season 7, the final of the series.
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"I don't think anyone's ready for the finale. It's really gonna hit you where it hurts. It's such a beautiful ending to this show. I'm just grateful I got to be part of it," Osment told ET ahead of the "Young Sheldon" finale.
Osment's time playing Mandy didn't end with "Young Sheldon" — in 2024 it was announced that the spin-off would be getting its own spin-off. "Georgie and Mandy's First Marriage" was picked up for a fall 2024 premiere. "I assume it starts right where we left off, so there isn't too big of a gap for our viewers in terms of, like, story or missing us too much. We just pick right up where we were," Osment dished to ET of the presumed storyline for the series.
Emily Osment got engaged
After heartbreak came love for Emily Osment. In June of 2023, the former child star shared via social media that she and her boyfriend — who goes by Jack Anthony on Instagram — were engaged. "I did not know life could be this sweet or I could ever be this deliriously happy. I am so proud of the life we have built together and the people we have become over the last few years. This love is so big and so uniquely ours and I know it can do anything," Osment captioned her Instagram post.
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The couple were apparently on a trip to Yosemite National Park when Anthony popped the question. And fans were taken with Osment's unique engagement ring — the actor was given a Toi et Moi ring, a unique setting that pairs two stones side by side, one of which is typically a diamond.
Anthony keeps a relatively low profile compared to his fiancée, but he seems to be a man of many talents. He posts music to SoundCloud under the name Farnia, and he makes a living as a partnerships expert for Linktree. Prior to their engagement, Osment paid tribute to Anthony on his birthday. "He walks into each day with kindness and silliness and a lust for life. we should all be a little more like him," she said on Instagram.
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She returned to the music scene under a stage name
As noted, Emily Osment is a multi-talented artist who's acted and released music. Osment took a long hiatus from music after releasing music under her given name during her "Hannah Montana" days, and in 2019, she returned to the scene under the stage name Bluebiird. The artist released some singles, including "Black Coffee Morning" and "When I Loved You," but her musical efforts were once again interrupted by other projects. "How can you focus on all of those at once? You can't. So sometimes things get put on the back burner. And unfortunately, Bluebiird did get put on a back burner for a while," Osment told Peoplein April 2024.
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After wrapping her work on "Young Sheldon," Osment released another single, "Porcelain Doll." With a little more time for other creative ventures, Osment intends to write and share more music. "Music was always something I loved and I never felt pressure to make it a career, just because it was such a hobby," she said. "Acting, of course, has just been my job for so long, and I love it, and it's brought me such joy and such friendship. It's been so lovely to have both, but there are things that take precedence sometimes." Fans will just have to stay tuned to see what she creates next.
