Cynthia Bailey

Bailey appeared in the 1985 low-budget film The Dark Power and the 1989 music video for New Order's "Round & Round".[11][12] In 1990, she played Roxanne in the film Without You I'm Nothing, and remained friends with its star Sandra Bernhard.[13][14] Naomi Campbell was considered for the role.[10] Bailey appeared in a 1990 episode of the sitcom The Cosby Show.[13][15] Her audition for a role in the 1991 film The Five Heartbeats was featured in the 2018 documentary The Making of the Five Heartbeats.[16] In 1993, she played a model in the film For Love or Money,[14] and the following year, she appeared in the music video for Heavy D's single "Nuttin But Love" from the album of the same name.[17] She played a masseuse in a 1995 episode of New York Undercover.[13]

After working as a runway model in Paris and Milan for a year, Bailey returned to New York City and modeled for Maybelline, Oil of Olay, and Target and in magazines including Vogue, Glamour, Elle, and Vanity Fair.[7][10] She appeared on two Essence magazine covers in June 1995 – her first job as a model – and 1997.[10][18] The magazine's then editor-in-chief Susan L. Taylor described Bailey as one of her favorite models.[10] Bailey's favorite modeling job was a Vanity Cover shot by Annie Leibovitz and featuring Iman, Beverly Johnson, Naomi Campbell, and Tyra Banks;[7] Iman had invited Bailey to participate in the shoot.[19]

In 2010, Bailey joined the Bravo reality television show The Real Housewives of Atlanta, which featured her relationship with club owner Peter Thomas and her friendship with NeNe Leakes.[10] She was introduced in the show's third season along with Phaedra Parks.[20] Bailey was initially uncertain about joining the show, describing it as "too dramatic", but changed her mind after viewing it as a business opportunity. She was contacted by Bravo shortly after moving to Atlanta with Thomas; the network said that they "wanted to bring more class to the cast, and feature more women that already had successful careers before the show".[2]

In 2011, Bailey opened her modeling school, Bailey Agency School of Fashion in Atlanta;[2][5][8] the following year, she held a model search in several cites in the Southern United States as part of a contest to win representation by a New York modeling agency.[5] Bailey appeared in a trilogy of music videos ("Age Ain't a Factor", "Baby x3", and "Chase Forever") for Jaheim's 2013 album Appreciation Day.[21][22][23] In the "Age Ain't a Factor" video, she was shown in a fictional Essence article on "Ageless Beauty", alongside LisaRaye McCoy and Vivica A. Fox.[21] The "Baby x3" video focuses on infidelity with Bailey and Thomas portraying "secret lovers".[22]

Bailey appeared in the 2015 documentary series Black Friday, which is about how little consumer spending is retained within black communities.[24] The same year, she acted in Kenya Moore's television pilot, Life Twirls On.[25][26] For the character, she used a Jamaican accent.[13] In 2016, she had a minor role in the film Sharknado: The 4th Awakens,[26] and guest starred on The Next :15 alongside former The Real Housewives of Atlanta costar Claudia Jordan.[27] She was featured on a celebrity edition of Cupcake Wars with Nene Leakes.[28]

Bailey was a guest judge for the preliminary and finals competition of the 65th Miss Universe competition.[29] In 2018, Bailey signed a contract with the New York-based agency Major Models; her daughter is also signed with the company.[9] In April 2018, Bailey underwent surgery to remove a lipoma tumor from her left shoulder blade. The procedure was successful without any reported complications.[30] In 2019, Bailey guest starred in an episode of Last Call,[31] and acted in How High 2, the sequel to the 2001 film How High.[14] She started a line of bags, named CB VIOR,[18][32] as well as a line of candles, leather goods, and eyewear.[18]

Bailey opened a wine bar, The Bailey Wine Cellar, and an event space, The Bailey Room, in Grant Park, Atlanta in July 2019.[33][34][35] The same year, she had a partnership with Seagram, creating a signature drink, a Bellini cocktail.[34][36] It was sold in April 2019. The launch party was shown on an eleventh season episode of The Real Housewives of Atlanta. In it, Leakes is angry that Bailey had invited Kenya Moore to the event without her knowledge.[34] The incident was discussed during the season's reunion episodes,[37] and Leakes and Bailey publicly ended their friendship.[38] Bailey is a brand ambassador for Seagram since 2018.[39] In 2019, she guest-starred on Star and Tales.[14][40]

Bailey chose to leave The Real Housewives of Atlanta in 2021, after being a part of the series for eleven seasons.[41] She starred in the first season of The Real Housewives Ultimate Girls Trip, a spin-off featuring various women from The Real Housewives franchise, which premiered on Peacock in 2021.[42][43] In an Essence interview conducted in the same year, she said she was shifting her focus from reality television to acting.[39] Bailey had a recurring role in the second season of Games People Play as documentarian Ndasia.[44]

In 2022, Bailey competed as a HouseGuest the third season of Celebrity Big Brother, placing third in the competition.[45] The same year, she appeared in the 2022 Lifetime movie Cruel Instruction.[46] The following year, Bailey returned to The Real Housewives of Atlanta as a guest for its fifteenth season.[47]