Who Is Really In Britney Spears' Inner Circle?

Many of us remember a time when "Baby One More Time" was bumping through our Sony Walkmans. The vision of a pony-tailed Britney Spears in a schoolgirl uniform still lives in all of our heads, due to the timeless success that Spears has achieved throughout her career. The artist went from living in a Louisiana trailer park to being the poster child of pop music — thanks to her grit and determination to break out of her small-town mold. She did just that, cementing her status as a legend in the music industry — with several chart-topping albums, successful world tours, and, well, Las Vegas residencies.

Under the harsh eye of the limelight, the Grammy-winning artist has gone through many ups and downs throughout her career and personal life. Her mental health was highly criticized for years, with paparazzi trolling her every move for a front-cover story. We've seen her fall in and out of love, become a mother, and enter a hugely contested conservatorship that lasted for 13 years. Throughout it all, Britney managed to continue releasing hits, embark on sold-out tours, judge X-Factor, and maintain her media appearances. 

Somewhere along the way, however, "Free Britney" supporters picked up that something wasn't right. Spears was silently pleading to be released from her legal bind for a decade, unbeknown to the public. Now that the conservatorship has ended, Britney is enjoying her freedom as the manager of her own person. With that said, she is selective with her friends. With her trust in her family broken, who is really in Britney Spears' inner circle? Read on to find out. 

One of the closest people to Britney Spears during her career was her long-time assistant Felicia Culotta. While Culotta remained behind the scenes during the majority of the time she worked for the star, she first came forward during Spears' legal troubles in the documentary "Framing Britney Spears." In the film, the former assistant admits that she's been close to Spears since the singer was five years old. Spear's mother Lynne couldn't juggle her daughter's career as well as raising her sister Jamie, so Culotta took on the role of chaperone for the "Lucky" singer when her career started making waves. Over time, that role began to be defined as an assistant, and Culotta accompanied Spears in all her commitments during the height of her career. 

Culotta spoke out during Spears's battle for legal freedom, writing on a fan website (via Today), "I cherish ALL the incredible opportunities that came my way thru my job with Britney and am crushed/saddened/heart sick by the way her life is unfolding," adding, "There's just so much you can do to help a person — I don't dare want to be an enabler, and I cannot love her enough for the both of us. I cannot convince her in ANY way to love herself." Spears's former assistant admitted that she attempted to reach out to the singer during her court battles without success. But, as previously reported, a whistleblower claimed that Spears was often blocked from communicating with the outside world due to restrictions by her father and former conservator.

It's no secret that perhaps the closest person to Britney Spears is her husband Sam Asghari. The pair first met after Asghari starred in Spears's music video for her track "Slumber Party," and Spears later contacted him. "I was like, 'He was really cute, this guy was really cute,' so I called him," the "Lucky" singer said in an interview with AMP 103.7's Fast in the Morning with Nathan Fast and Sybil Summers (via People.) Spears was thankful she found his number in a bag five months after they met, adding, "He's just a really fun, funny person." The duo went on to have a romantic relationship for years which included lots of Instagrammable Hawaii vacations and couple workouts together. They tied the knot in 2022 in an intimate ceremony in front of their closest friends.

Asghari is Iranian, and he came to the United States in 2006 to pursue his dreams of acting. As per his IMDb page, he's appeared in TV Series like "Black Monday" and "NCIS" in addition to being Spears's "Slumber Party" love interest. He keeps himself busy in the gym as well, and he currently runs his own personal training company. "Asghari Fitness"  which offers customized meal plans and workouts.

Asghari had nothing but good things to say about his wife after meeting her for the first time. He revealed that he was smitten upon seeing her, saying, "It was the humbleness that attracted me," adding "She was very humble and she had a beautiful soul."

Britney Spears has a true friend — and custom fashion designer — in Donatella Versace. The fashion icon revealed that she's been tight with the "Oops I Did It Again" singer for decades when she came on as a guest for the "High Low with EmRata" podcast. "I think the first designer ... she met in her life was me," she revealed. "She came to Milano, she was like 20 or 21 ... she was at the height of her career, but she was so humble." 

Versace was one of the exclusive guests in attendance at Spears's nuptials, and custom designed the gown the singer wore to say, "I Do." The classic gown was a labor of true love taking more than 700 hours to make and encrusted with pearl buttons, a nearly 10-foot-long train, and a corset bodice that gave way to a portrait neckline. The "Toxic" singer went on to wear three more custom-made Versace dresses for her reception. "It was amazing to see Britney, so liberated, so free," Versace said of the ceremony, adding, "The wedding was very small, but very beautiful."

Versace came forward to congratulate the singer on her newfound freedom following her conservatorship in a sweet Instagram post dedicated to Spears. "Freedom is a human right. My heart is smiling for you, Britney. Congratulations on your regained and deserved emancipation. I love you, your fierce fans love you and the world NEEDS your brilliance. Happy Britneypendence day!" the designer wrote alongside a photo of the two of them. 

Britney Spears keeps her exclusive girl gang close, and without a doubt, Drew Barrymore makes the cut. "I made friends with Britney about a year and a half ago, and we sort of had some secret exchanges. And I know that sounds nefarious. It was exactly the opposite," the actor said on "The Tonight Show Starring Jimmy Fallon." The Charlie's Angel star went on to admit that they each have been through similar things in life, so they had a natural connection and friendship. 

"The feelings of growing up, struggling, all the stuff that we've both gone through is something that I felt connected to her [about]," Barrymore revealed on the show. "And I'm not a real reach-out kind of person, you know, I'm not Hollywood Bob, I'm not slick." Barrymore admitted she felt the need to connect with Spears in the midst of her legal battle because she felt empathetic to what the singer was dealing with. "We found a deep connection there," Barrymore confessed. "There's a human being at the center of this, so we made friends. Like, genuine friends."

Barrymore was in attendance at Spears's wedding to Sam Asghari, alongside legends like Madonna, Donatella Versace, and Paris Hilton. "It was intimate, it was fairy tale-ish. It was very sweet, there was no press. It was the way [Spears] wanted to do it," Barrymore said. "She did the ceremony, we got right to the dance party. We had the best time."

Selena Gomez was also on the exclusive guestlist for Britney Spears's tight-knit wedding ceremony. The "Calm Down" singer went on "Jimmy Kimmel Live" where she was pressed for details about the ceremony. "I am really happy for her, it was beautiful," Gomez admitted. Spears gushed about Gomez in an Instagram post following the ceremony, writing, "So many incredible people came to our wedding and I'm still in shock  !!! [Drew Barrymore] my girl crush and [Selena Gomez] who btw is way prettier in person if that's possible both came !!! I was speechless ..."

It isn't the first time the "Gimme More" singer has sung Gomez's praises. She also posted a since-deleted Instagram photo (per Billboard) of the "Come & Get It" singer's rose back tattoo, writing, "I'm not really into tattoos but dear God ... how beautiful is this?" adding, "[Selena Gomez] has inspired me to get another one!" 

No one can forget the iconic kiss between Madonna and Britney Spears during their 2003 VMA performance. But fans may be surprised to know that the music legends are still close two decades later. Madonna was one of Spears's biggest supporters during her conservatorship battle, speaking out in a since-deleted social media post (per Grazia Magazine.) "Death to the greedy patriarchy that has been doing this to women for centuries," the "Like A Virgin" singer wrote. "This is a violation of human rights! Britney we [are] coming to get you out of jail!"

At Spears's nuptials, following her recent liberation from lengthy conservatorship — there was finally cause to celebrate. Madonna and Spears recreated their famous VMA kiss following the ceremony and were seen giving each other a hug on the dance floor. "Britney you look so happy and in love," Madonna wrote in a since-deleted Instagram post. "I wish you and Sam all the best ! Last night was fun and sweaty!!"

It's a full circle moment for the "Womanizer" singer, who has admitted early on in her career the role Madonna played for her. "My first memories of Madonna I think when she did 'Like a Virgin.' Oh my goodness, honestly, I remember watching her videos and saying, 'I wanna do that one day," Spears said on the Oprah Winfrey Show. "She's a true artist. She is the pop icon. She's like the pioneer of all women," she added.

Britney Spears welcomed her first child Preston with her ex-husband Kevin Federline in 2005, and her second son Jayden the following year. Over the years the "Overprotected" singer has been criticized heavily in the media for her parenting, but there's no question that Spears loves being a mom. Though her custody agreement has Federline keeping the kids more often in a 70-30 split, Spears shares sweet moments with her sons whenever she gets a chance. 

The "Toxic" singer took her kids out for a day at the Van Gogh art exhibit in 2021, writing on Instagram, "My children and I went to [sic] the amazing @vangoghla"... it was so freaking cool ... I obviously don't get out much so I was pretty excited  !!!" However, spears' relationship with her children has been through its ups and downs. Her son Jayden spoke out in a 2022 interview (via Daily Mail) saying, "I 100% think this can be fixed. It's just going to take a lot of time and effort. I just want her to get better mentally. When she gets better I really want to see her again," Jayden admitted. 

Jayden also admitted that he and his brother Preston chose not to attend their mother's wedding to Sam Asghari, in which Spears excluded her family following her bitter conservatorship battle. "I'm really happy for them, but she didn't invite the whole family and then if it was just going to be me and Preston, I just don't see how that situation would have ended on good terms," Jayden said.

Britney Spears' former assistant Victoria Asher is tight with the "Baby One More Time Singer," even going on Hawaiian vacations with the star. Asher, who goes by "Vicky T," is a songwriter and keytarist for the band Cobra Starships. "Yep ... me naked in the pool and my assistant @vickyt holding me like a baby!!!! BAHAHAHAHA," Spears wrote in an Instagram post featuring her and Vicky T. 

The former assistant worked for Spears amidst her legal battles, and the two frequently posted photos together on social media. "She's a shining light. Nothing but love for this special human @britneyspears," Vicky T wrote on Instagram. When the "Brave New Girl" artist was finally freed from the conservatorship in 2021, her friend had nothing but kind words of support for the star. 

In an Instagram Live, Vicky T answered fans' lingering questions following Spears' newfound freedom. "She has written me some very beautiful texts and we were supposed to get dinner but we didn't yet. But I am always there for that woman," the former assistant said (per Pop Sugar.) Vicky T went on to say she's just a phone call away if Spears needs her, adding, "I know how much all of you love her and I know how much all of you are curious about things. I would love to continue answering your questions but [out of] respect for her, I'm not going to talk on her behalf."

The man credited with freeing Britney Spears from her 13-year-long conservatorship is Mathew Rosengart. The singer thanked her lawyer and expressed her gratitude for his work via Instagram, writing, "This man has turned my life around ... So many exciting projects ahead !!!! We accidentally matched for lunch !!!! Thank you for being so kind and respectful to me always!!!!!! Pssss Mathew Rosengart ... I simply adore you !!!!"

Rosengart came into Spears' life after he listened to the shocking audio of her court testimony, in which the public got a glimpse of her side of the story for the first time in more than a decade. "Listening to Britney's own June 23 court testimony, which was before I was involved or retained, I heard the voice of a woman who had been bullied," Rosengart told Variety. In the audio, Spears revealed her difficulty trusting her own lawyer at the time, one that neglected to inform her she could petition to terminate the conservatorship. "I was concerned that she had been deprived of certain civil or fundamental liberties, even as she was earning hundreds of millions of dollars as a performer, from which others were benefitting," he said of the legal bind. 

Following the November 2021 ruling of the end to Spears' conservatorship, Rosengart spoke out after leaving the courthouse. "Britney, as of today, is a free woman," he added, "I thank her for her courage and poise and power and for our relationship."

Britney Spears had nothing but good things to say about Kate Hudson. The Grammy-winning artist took to Instagram (per Billboard) to share her gratitude for Hudson and Drew Barrymore and her writing, "They are by far the 2 most beautiful people I have ever seen in my life." Spears went on to say, "I had to open my stupid mouth with Kate so I ran away immediately," she admitted of the first time she met the actor. "Although I love my husband I will be honest and say I get annoyed all the time. So I think sisterhood is actually profound with one another." 

Spears went on to admit in the social media post that she misses the simple act of smiling at strangers, something she says she feels strange about doing now. Hudson offered some sweet words for the singer, writing, "DON'T EVER STOP SMILING AT STRANGERS [sic]! You can and have changed lives with that smile!" She also commented how flattered she was by the "Oops I Did It Again" singer's words.

Spears reposted a video the "Glass Onion" star sent her featuring her and her brother singing "Happy Birthday" to Spears. The two have been close for years, with Hudson posting an Instagram photo alongside the star in 2016, writing, "That moment when @britneyspears shows up to your game night and your all like #itsbritneybitch."

No one can forget the iconic days of the early 2000s when paparazzi trolled Britney Spears, Paris Hilton, and Lindsay Lohan on their wild nights out clubbing. Fast forward decades later and the "Toxic" singer is still close with the "Simple Life" star. In a 2021 interview with Andy Cohen for Sirius XM Hilton admitted that she's one of Spears' biggest supporters, revealing that she didn't agree with the conservatorship.

"I saw her this summer. We've had dinners, I saw her in Malibu. I just love her so much," said Hilton. "She is so sweet and so innocent and such a nice girl. We just talk about happy things. Music, fashion ... fun things. I never like to bring up negative things and make people feel uncomfortable so I've never talked about [the conservatorship] with her." She went on to add that she feels Spears should be able to have control of her life and that the legal bind she was under made no sense given her status as a pop icon.

Hilton and Spears celebrated the singer's newfound freedom at Spears' wedding. The "Simple Life" star performed "Stars Are Blind" alongside the "Toxic" singer in a duet. "It was a magical fairytale," Hilton told E! News of the ceremony. "I'm so happy for her. She's like an angel. And it was just an iconic night with so many incredible powerful women and we had the most epic night ever."