At the age of 17, producer C.V. Ramakrishna Prasad, offered Waheeda Rehman a dancing role in his film, Rojulu Marayi (1955). Prasad knew her father, and Rehman appeared in only one dance scene in the film, performing the song "Eruvaka sagaro ranno chinnannaa.” The Telugu language film starred Akkineni Nageswara Rao and Sowcar Janaki, and the title translated as 'The Days have Changed'. The days did indeed change for Rehman as the song became immensely popular and her vivacious screen presence was noted. The film was remade in Kannada as Kaalam Mari Pochu (1955).

Following the success of her first film, Waheeda Rehman had a fortuitous meeting with Guru Dutt, which would change the course of her life forever.

Guru Dutt was visiting Hyderabad, and sitting in a distributor's office one day, he heard some commotion outside. The distributor explained that the noise was that of excited fans cheering the stars of the popular Telugu film, who happened to be passing by. He added that a 'new girl,' Waheeda Rehman, had performed a song in the film, which had become a sensational hit. Upon hearing her name, Dutt enquired if she spoke Urdu and requested for a meeting as he was looking for fresh faces for his upcoming film.

The following day, Dutt met Rehman and asked only a few questions in Hindi. Three months later, he sent a representative to Chennai to bring Rehman to Mumbai.

Guru Dutt wished to sign Waheeda Rehman for a three-year contract which became contentious as there was a demand to change her name, which was seen as being too long. Dutt's assistant at the time, Raj Khosla, suggested that a screen name be adopted but upon Rehman's refusal, and a lot of back and forth, the demand was dropped.

Even though Rehman was just 17 years old at the time, she demanded that her contract contain an explicit clause ensuring that she would not be asked to wear any costume that she was not comfortable wearing. This was extremely unusual at the time and reportedly, Khosla thought that the actor was being too demanding but after some back and forth, Dutt conceded and added the clause.

This unusual clause was brought into play during the filming of Rehman's Hindi film debut, C.I.D. (1956). For the song, “Kahin pe nigahein kahin pe nishaana”, she was required to wear a long-sleeved lace blouse with a long skirt. As the blouse had no lining, Rehman felt that it was 'see through' and raise an objection to wearing it. Director Raj Khosla was quite irritated with this, and several people tried to convince her to let it go but to no avail. Ultimately, Guru Dutt was called to sort out the matter and although he did not see the problem with the garment, he honoured Rehman's choice in the matter. Costume designer Bhanu Athaiya could not add a lining at the last moment, and so Rehman suggested wearing a dupatta over the blouse, which finally resolved the situation.

Waheeda Rehman played the role of a gentle vamp in C.I.D. (1956), and the film became immensely popular, catapulting her to stardom. The film celebrated its silver jubilee and Rehman, who had signed a three-film contract with Guru Dutt Films, went on to shoot for the next film, Pyaasa (1957).

Pyaasa (1957), Waheeda Rehman's second Hindi-language film, saw her playing the role of a sex worker, Gulabo, and although stars like Nargis and Madhubala were vying to play the role, it was Rehman who had signed the contract with the studio, and thus bagged it.

An exploration of love and human values, the film offers a critique of materialism. The central character, Vijay, is a poet, who realizes that the recognition he so dearly craved has no value because people only paid attention to his social standing, not him as a person. Captured in the powerful lyrics of the song, “Ye duniya agar mil bhi jaaye”, the film wielded Sahir Ludhianvi's lyrics as foundational to the film and its emotion.

Pyaasa was pivotal to Rehman's career as it made people take note of her talent. Rehman was nominated for a Filmfare Award in a supporting role, but Guru Dutt famously withdrew her nomination as he felt that her role was that of a second leading lady, and not a supporting one.

Waheeda Rehman's next major professional step came with the film, Solva Saal (1958). This was her first film outside of Guru Dutt Films, and although under a contract, Dutt allowed her to take up outside work, as he believed that female actors usually had a short screen life.

Directed by Raj Khosla, and co-starring Dev Anand, the film was significant for both personal and financial reasons for Rehman. She received a sum of 30,000 rupees for Solva Saal, which was a substantial increase when compared with the monthly salary she was receiving as part of her contract with Guru Dutt Films. However, once again, she locked horns with Khosla over a costume. The costume department gave her a chiffon saree and a strapless blouse to wear but Rehman refused to wear it, as she felt that her character, named Lajwanti, had a name that signified modesty, and thus, would not wear such a costume in front of a stranger (Dev Anand's character in the scene). Khosla was furious but ultimately, Rehman wore a different blouse with the saree and the shooting continued.

While shooting for the film, however, Rehman suffered a terrible personal loss as her mother, Mumtaz Begum, suffered a massive stroke and passed away. Her death came as a shock to the family, especially as she had lost at a very young age.

The first CinemaScope film made in India, Kaagaz Ke Phool (1959), remains a milestone in the acting career of Waheeda Rehman. Directed by Guru Dutt, and starring him in the lead role, the narrative follows the life of a film director Suresh Sinha (Guru Dutt), who falls in love with a young, upcoming actress, Shanti (Waheeda Rehman).

Seen as being Dutt's most autobiographical film, it was also the film that devastated him as the film received dismal reviews upon its release and did not do well commercially. However, years later, the film gained its due recognition and is considered a classic.
The stunning cinematography remains iconic to this day, and the songs, especially “Waqt Ne Kiya Kya Haseen Sitam” is studied across the world.

After the dismal reception of Kaagaz Ke Phool (1959), Guru Dutt decided to switch gears in order to recover some of the losses incurred by the commercial failure of the film. The film's failure had also made him resolute to never direct a film again, and so for the next film, M Sadiq was chosen as the director.

Based on a story by Saghar Usmani, 'Ek Jhalak' (A Glimpse), Chaudhvin Ka Chand (1960), featured Dutt and actor Rehman, along with Waheeda Rehman, in the lead roles. The Muslim social became a big commercial success, and in fact, Dutt shot the title song in colour. This was considered a tactic to entice audiences to the theatres, and it certainly worked.

Following the success of Chaudhvin Ka Chand (1960), Waheeda Rehman's career was marked by artistic and commercial diversification.

She starred in Satyajit Ray's Abhijan (1962), which was a major artistic shift. Ray approached her for the film, and she considered the casting to be an honour. Working with Ray demanded a different approach, as he was known for his meticulous preparation. He provided Rehman with a bound script, a rarity at the time, along with an audio tape of her dialogues. Dedicated to creating a realistic effect, he even requested her to sing her lines in one scene herself, rather than mime to a playback singer, as he felt that the slightly imperfect voice of Gulaabi, a simple village girl, would sound more natural, and thus better suited to the effect that he wished for.

The central character in Abhijaan, is believed to have influence filmmaker Martin Scorsese, to create his most iconic character, Travis Bickle (played by Robert DeNiro) in Taxi Driver (1976).

In 1962, Waheeda Rehman starred in the horror/mystery film Bees Saal Baad (1962). An adaptation of Sir Arthur Conan Doyle's The Hound of the Baskervilles, the film marked the debut of actor Biswajeet in his first Hindi film role. Directed by Biren Nag, the film was a commercial success. The move to the suspense genre was quite exciting for Rehman, who enjoyed working in the film.

The classic film, Sahib Bibi Aur Ghulam (1962), was not an easy choice for Waheeda Rehman, who had become a sought-after star by this time. The film features Meena Kumari in the lead role, alongside the male leads Rehman and Guru Dutt. Waheeda Rehman felt that her role, Jabba, was a supporting one and was reluctant to accept it. However, she ultimately as she did not want people to assume that she had refused the role because the film was being directed by Abrar Alvi.

The final scene of the film, where Jabba is waiting for Bhoothnath (Guru Dutt) outside the ruins of the haveli (mansion), marked the last time that Waheeda Rehman and Guru Dutt worked together.

Another significant film in Waheeda Rehman's career was Mujhe Jeene Do (1963). A story about a dacoit and a dancer, the film was amongst the highest-earning films that year. Rehman played the character of a sex worker, Chamelijaan, a role that required portraying a range of emotions, from that of a dancing girl to a wife and protective mother.

The film drew heavily from real-life events and was shot in the dangerous Chambal ravines, where the unit had police protection. There were threats from real life dacoits during the shooting of the film and in one incident, cast members had to be quickly evacuated from the sets, for fear of being attacked.

Waheeda Rehman's next significant moment came with the film Guide (1965). Directed by Vijay Anand and starring Dev Anand, the film was based on R.K. Narayan's eponymous novel, and was intended to be shot simultaneously in both Hindi and English. The English version was directed by American director, Tad Danielewski.

Rehman played the role of Rosie, a rather unusual character, not seen in Hindi cinema at the time. Rosie was the daughter of a sex worker who gained respectability in society by marrying a wealthy man but she had to sacrifice her love for dance in the bargain. A married woman, she leaves her husband to go and live with a local guide, Raju (Dev Anand), who becomes her lover.

Rosie's character was that of a modern, respectable woman and not that of an immoral woman who leaves her husband to take on a lover. Although she displays strong agency by slapping her husband and walking out on him, she later also leaves her lover when his behaviour towards her starts to deteriorate.

The English screenplay was written by Pearl S. Buck, who instructed Rehman to use her natural Indian accent and speak her own English lines in the film. One of the highlights of the film are its songs, and choreography, amongst them being the snake dance performed by Rehman.

The critical acclaim and popularity of the film earned her the Filmfare Award for Best Actress, along with the Best Actress award at the Chicago Film Festival in 1965 for the English version of the film.

Teesri Kasam (1966), based on the story 'Maare Gaye Gulfaam', was directed by Basu Bhattacharya and starred Waheeda Rehman and Raj Kapoor in the lead roles. This was Rehman's second film with Kapoor, as the two had previously worked together on Ek Dil Sau Afsane (1963).

Rehman starred as Hirabai, a nautanki girl, and Raj Kapoor played a bullock-cart driver, Hiraman. Bhattacharya encouraged both actors to perform in a natural style, and the film was shot in a small town near Bhopal, to enhance the realism of the film.

Waheeda Rehman received the Silver Medal award at the National Film Awards in 1966, for her performance. The film was also screened at the Moscow Film Festival in 1967.

Waheeda Rehman played a double role in Ram Maheshwari's Neel Kamal (1968). She co-starred with Manoj Kumar and Raaj Kumar in the film. Rehman was asked to wear blue contact lenses for the film as it was all the rage at the time. Besides, the title of the film Neel Kamal (Blue Lotus) corresponded to the fashion trend. However, Rehman refused to do so just for the trend.

The film was a major commercial success, and Rehman won the Filmfare Award for the Best Actress.

Waheeda Rehman continued to balance her commercial film roles while simultaneously playing characters with a degree of complexity and nuance. One such film was Asit Sen's Khamoshi (1969), where she starred alongside Rajesh Khanna.

Based on a Bengali short story, the black and white film is remembered for its cinematography by Kamal Bose, and memorable music by Hemant Kumar.

Rehman played a psychiatric nurse, Nurse Radha, in the film. Her character was required to express intense but suppressed feelings, a challenge for Rehman, who was drawn to the portrayal of quieter emotions. Although Rehman worked with Asit Sen, only in this film, she considered him to be one with a great understanding of cinema and was guided by him to deliver the correct tone for her character.

On 26 July 1974, Waheeda Rehman married actor Kamaljeet Rekhy (Shashi) and relocated to Bangalore, where they lived on a farm. During this time, she focused on raising her children, Sohail, and Kashvi. Owing to this hiatus of sorts, she transitioned into character roles, which, in the long term, ensured her longevity on the screen.

Kabhi Kabhie (1976) directed by Yash Chopra, featured a large ensemble cast which included Shashi Kapoor, Amitabh Bachchan, Raakhee, Rishi Kapoor, and Neetu Singh. Waheeda Rehman played the role of Bachchan's wife, Anjali Malhotra in the film, and received a Filmfare Award nomination for Best Supporting Actress. In fact, she was the first to sign the film, and Chopra is the one who advised her not to play the role of Bachchan's mother in Deewar (1975), as she was playing his wife in Kabhi Kabhie. However, she did end up playing his mother a few years later in Trishul (1978).

Directed by Yash Chopra and written by Salim-Javed, Trishul (1978), once again, brought together an ensemble cast featuring Shashi Kapoor, Sanjeev Kumar, Amitabh Bachchan, Hema Malini, Raakhee, Poonam Dhillon, and Waheeda Rehman. Once again, Rehman played a daring role, that of a single mother, Shanti, a character not quite explored in mainstream cinema at the time.

Although the role was a guest appearance, it highlighted the social stigma faced by single women and attempted to humanise their situation. The dignity which Rehman brought to the character of Shanti is seen as being pivotal in redefining character roles for actresses. It also solidified her career transition into playing challenging character roles, which included playing the mother to actors who were previously cast as her romantic leads!

Through the 1980s, Waheeda Rehman continued to play character roles in films expanding her repertoire. Some of these include Gulzar's Namkeen (1982), which won her a nomination for Best Supporting Actress at the Filmfare Awards. Prakash Mehra's Namak Halaal (1982), Manmohan Desai's Coolie (1983), K Raghavendra Rao's Himmatwala (1983), Yash Chopra's Mashaal (1984), and Yash Chopra's Chandni (1989). Chandni won her another Filmfare nomination for Best Supporting Actress, as did the next Yash Chopra film, Lamhe (1991).

The noughties saw Waheeda Rehman continuing to star in supporting roles, straddling mainstream and alternative cinema. Deepa Mehta's Water (2005), Aparna Sen's 15 Park Avenue (2005), Rakeysh Omprakash Mehra's Rang De Basanti (2006), Rakeysh Omprakash Mehra's Delhi 6 (2009), Anup Singh's The Song of Scorpions (2017), Vishwaroopam II (2018), are some of her notable films during this period.

She was presented with the Padma Bhushan award in 2011.

Waheeda Rehman's legacy is defined by her artistic integrity, her dedication to take on challenging roles, and her contribution to several classic films of Indian cinema. Renowned for her subtle screen presence and natural acting style, her career includes some of the most iconic films of Indian cinema. From Guru Dutt to Satyajit Ray, Chetan Anand, Gulzar, and Yash Chopra, she worked with a wide range of acclaimed directors through her career, successfully transitioning from playing a lead actress to complex character roles. Her willingness to accept unconventional supporting roles, and guest appearances ensured her professional longevity, and she continued to work in films long after many of her contemporaries retired from the silver screen.

In 2021, she was honoured with India's highest award in the field of cinema, the Dadasaheb Phalke Award.