Breakthrough and struggles (2005-2010) Singh began her career as a model before making the transition to the silver screen. After completing her graduation, she began modelling. She later drew attention after performing in the music video
Sunset Point by
Gulzar, followed by a music video with
Abhijeet Bhattacharya. Singh made her film debut with
Sudhir Mishra's
Hazaaron Khwaishein Aisi in 2005. The film received critical acclaim and was a box office average. Singh played Geeta, a college student and social worker opposite
Kay Kay Menon.
Sukanya Verma stated, "Chitrangada is definitely someone to watch out for. She is a complete natural who zaps the camera with a passionate performance." John Pancake of
The Washington Post noted her for giving "her character a deep sense of dignity and decency." Her next release,
Kal: Yesterday and Tomorrow was a critical and commercial failure. Following a three year hiatus, Singh returned to films opposite
Sanjay Suri in
Onir's
Sorry Bhai!. Its release over the weekend of the
Mumbai terror attacks and was a failure at the box office. This failure led to another two years break from acting.
Commercial films and fluctuations (2011–2020) Singh started 2011 with Sudhir Mishra's
Yeh Saali Zindagi, where she played a club singer Priti opposite
Irrfan Khan. Despite positive reviews, it emerged an average grosser.
Rajeev Masand noted, "Chitrangada uses her smouldering looks to create a mysterious character whose motivations and actions are unclear." Singh then played Tanya, an economics professor opposite
Akshay Kumar in Rohit Dhawan's
Desi Boyz.
Taran Adarsh stated, "Chitrangada looks stunning and acts well, but her character isn't convincing." The film emerged a moderate success. In 2012, she performed a dance number in
Shirish Kunder's
Joker. Singh had three releases in 2013. She first appeared as a prostitute in the short film
Kirchiyaan. She then played an ambitious Maya opposite
Arjun Rampal in Sudhir Mishra's
Inkaar, which was box office average despite positive reviews. Rachit Gupta of
Filmfare praised her performance and chemistry with Rampal. Singh later played Anushka a career women, in Kapil Sharma's
I, Me Aur Main opposite
John Abraham, which was a box office failure. This was followed by a dance number in
Anjaan (2014) and
Gabbar Is Back (2015) and a special appearance in
Munna Michael (2018). Singh turned a producer in 2018, with the biographical sports drama film
Soorma, which was released under her banner C.S. Films and received positive response. She then played a mistress Suhani in
Tigmanshu Dhulia's
Saheb, Biwi Aur Gangster 3 opposite
Sanjay Dutt, which flopped at the box office. In her last film of the year, Singh played Mandira, a businessman's wife opposite
Saif Ali Khan in Gauravv K. Chawla's
Baazaar. That year, she also ventured into television as a judge with ''
DID Li'l Masters 4. With no release in 2019, she had a cameo appearance in Ghoomketu'' in 2020.
Career expansion and success (2021-present) In 2021, Singh played Mary, an assassin's wife opposite
Abhishek Bachchan in Diya Annapurna Ghosh's
Bob Biswas. Anuj Kumar of
The Hindu published, "Chitrangada gets a solid part as the ravishing wife of Bob. Though she doesn’t always succeed in shedding the uber-chic baggage, but her Mary shines among the wimpy men around her." In 2022, Singh expanded to
OTT with the anthology series
Modern Love Mumbai, playing Latika, an aspiring novelist opposite
Arshad Warsi. In 2023, Singh played Rukmani, a royal queen alongside
Vikrant Massey in
Gaslight.
Saibal Chatterjee stated, "Chitrangada plays a woman whose allure lies in her ability to mask her desires and secrets behind a benign facade. She pulls it off for the most part." Following this, Singh appeared as Kadambari, in a cameo appearance in
Khel Khel Mein. In her first release of 2025, Singh played the leader of opposition in the series
Khakee: The Bengal Chapter. Sugandha Rawal of
Hindustan Times took note of her "commanding performance", while several reviews criticised her faltered character. She then played a businesswoman opposite
Jackie Shroff in
Housefull 5. The film was released in two versions, titled
Housefull 5A and
Housefull 5B, each featuring a different climax and murderer. Devesh Sharma stated that she adds to the "glamour quotient", but has nothing to do in the film. In late 2025, Singh appeared opposite Salman Khan in the Hindi-language war drama film
Battle of Galwan, directed by
Apoorva Lakhia. The film is produced by
Salman Khan Films and is scheduled for theatrical release in April 2026. ==Personal life==