Cheung attended Rosaryhill School for secondary education in Hong Kong and, at age 12, enrolled at Norwich School in England. During his time at Rosaryhill, Cheung was academically poor but excelled in English. He discovered a newfound interest in Western films and immersed himself in music, studying the original soundtrack of Romeo and Juliet. When in England, he recalled that there were “racial problems”, but managed to make friends. During weekends, he worked as a bartender and would sometimes do amateur singing at his relatives’ restaurant in Southend-on-Sea. He came across the film Gone with the Wind and chose Leslie as his English name inspired by the actor Leslie Howard, feeling that “The name can be a man’s or woman’s, it’s very unisex.” Cheung attended the University of Leeds, where he studied textile management. After one year of study, in 1976, he returned to Hong Kong when his father became paralyzed on one side after a stroke. As the father wanted all of his children to be at home, Cheung abandoned his study and became a salesman for Levi’s for a living. Cheung recalled that during this time, “I had no plans; there I was, feeling like I was hanging in the middle of nowhere.”

Upon returning to Hong Kong, Cheung went back to high school as a mature student and formed a band, where he was the lead singer, with his classmates. In May 1977, the band members signed up individually for Rediffusion Television (RTV)’s Asian Singing Contest. Only Cheung remained until the final round of the Hong Kong division, where he finished as the first runner-up with a rendition of “American Pie”. He proceeded to the pan-Asian division, finishing fifth. Soon after the competition, RTV offered Cheung a three-year contract as a second-rate actor for RTV. He also signed with Polydor Records with hopes of releasing music albums.

In 1977, during the filming the RTV television series Love Story, the then 20-year-old Cheung met and fallen in love with his 17-year-old co-star, Teresa Mo (毛舜筠), and they got along after they finished the series. In 1979, Cheung proposed to Mo with flowers in marriage. But his sudden proposal startled Mo and she began to distance herself from him. Although Cheung and Teresa Mo eventually broke up shortly after the proposal and briefly lost contact, they later remained close friends again when they reunited for the 1992 film All’s Well, Ends Well.

Cheung later went into a brief relationship with an actress Shirley Yim [zh], the younger sister of Michelle Yim, but they broke up in 1980, due to their incompatibly for each other’s lifestyles.

Cheung signed with Capital Artists, a record label closely associated with the then-dominant television network TVB, in 1982. His first hit single, “The Wind Blows On” (風繼續吹; 1982), is a cover version of Momoe Yamaguchi’s Japanese single “The Other Side of Goodbye” (さよならの向こう側). The song was successful on charts, revitalising Cheung’s image as a Cantopop singer. The titular album was Cheung’s first to be certified gold by the International Federation of the Phonographic Industry (IFPI) Hong Kong. His second album with Capital, Craziness (一片痴, 1983), is a compilation of songs he recorded for TVB dramas. The album was also a success, receiving a gold certification from the IFPI Hong Kong. He continued his movie crossover with roles mostly in teenage films, and earned his first major recognition for starring in Nomad (1982). While Cheung had already been a well-known actor with likeable personae in TVB productions, his role as a disillusioned teenager in Nomad foresaw his future reputation as an icon of rebel. The role garnered Cheung a nomination for Best Actor at the 1983 Hong Kong Film Awards.

The year 1984 was when Cheung achieved mass stardom. He released the hit single “Monica”, a cover of the single by Japanese singer Kōji Kikkawa. The song topped charts in Hong Kong and was one of the 10 gold-certified songs honoured at TVB’s 1984 Jade Solid Gold Best Ten Music Awards and the 1984 RTHK Top 10 Gold Songs Awards. The song’s upbeat dance production introduced a new musical trend to Cantopop, in addition to the traditional sentimental ballads that had dominated the scene. Cheung’s 1984 self-titled album, which included “Monica”, was his first to be certified platinum by the IFPI Hong Kong and sold over 200,000 copies. He starred in the TVB drama Once Upon an Ordinary Girl (儂本多情) and the film Behind the Yellow Line. In the latter, he co-starred with actress Maggie Cheung and singer-actress Anita Mui. Both productions were commercially successful and put Cheung into the limelight as a prominent entertainer. As Cheung’s fame expanded, the media began to pit him against fellow singer-actor Alan Tam, as the two were the most successful male Cantopop singers as the moment. The publicised so-called rivalry contributed to Cantopop’s booming sales and lasted until the end of the 1980s.

In 1984, at the house of Albert Yeung, Cheung met Cindy Yeung (楊諾詩), the youngest daughter of Albert Yeung who had recently returned from Boston. Cindy Yeung was also a fan of Cheung and was seven years younger than him. Cheung and Yeung went out on several dates until the latter returned to Boston. They continued their relationship through phone calls and letters, but would later part ways on the following year but still remained good friends. Cheung felt that if he was not in showbiz, he may have already been married with children like most of his friends.

The turning point in Cheung’s acting career came in 1986 with his starring role in John Woo’s (吳宇森) A Better Tomorrow, which broke Hong Kong’s box office record. In the following years Cheung was praised for his performances in films which found popularity with audiences worldwide, including A Chinese Ghost Story (1987), Rouge (1987) and Wong Kar-Wai’s Days of Being Wild (1991).

Cheung’s career ascended to a new peak in 1987, when he released his first album under Cinepoly, Summer Romance. The album was the best-selling Cantopop release of the year, earning seven times platinum certification from the IFPI Hong Kong and sold over 350,000 copies. Its lead single, “Sleepless Night” (無心睡眠), won the Gold Song Gold Award at the 1987 Jade Solid Gold Awards. The next two albums, Virgin Snow and Hot Summer, both were released in 1988 and sold well, receiving gold and platinum certifications from the IFPI Hong Kong. He also had starring roles in the films A Chinese Ghost Story and Rouge. The performance of Cheung and his co-star Anita Mui in Rouge consolidated the pair’s reputation as the top Hong Kong entertainers. Yiu-wai Chu, author of the book Hong Kong Cantopop: A Concise History (2017), noted that Cheung and Mui formed an “unprecedented” chemistry showcasing “mystic power of charisma”, not only in films but also on stage performances together. The two were also close friends in real life.

Cheung embarked on a 23-date tour at the Hong Kong Coliseum in mid-1988, sponsored by Pepsi. The tour was a sold-out and accumulated over 250,000 spectators. He also held several shows catering to the Chinese community in North America, visiting Atlantic City, Calgary, Toronto, and Vancouver. In the wake of the intense political atmosphere in mainland China in the late 1980s, which would culminate in the 1989 Tiananmen Square protests, successful Cantopop singers announced public withdrawal from the music industry and emigrated to western countries. Cheung followed suit, announcing his “retirement” from Cantopop and emigrating to Vancouver, Canada in 1989. Prior to his retirement, Cheung released three further albums under Cinepoly—Leslie ’89, Salute, Final Encounter—all of which received platinum certifications from the IFPI Hong Kong. He won Most Popular Male Artist twice, at the 1988 and 1989 Jade Solid Gold Best Ten Music Awards. His “farewell concert tour”, in support of the album Final Encounter, ran for 33 consecutive sold-out shows at the Hong Kong Coliseum. Cheung donated profits of his 1989 album Salute to the Hong Kong Academy for Performing Arts, which was named the Leslie Cheung Memorial Scholarship after his death.

In addition to music, Cheung had his breakthrough movie role in the crime-action A Better Tomorrow (1986), which would pave the way for his upcoming career in cinema. Cheung announced his “retirement” and emigrated to Canada in 1989, in the aftermath of the handover of Hong Kong, but subsequently returned to show business in 1990.

He moved to Vancouver in 1990 and became a Canadian citizen by naturalization.

In an interview in 1992, Cheung stated that “My mind is bisexual. It’s easy for me to love a woman. It’s also easy for me to love a man, too” and “I believe that a good actor would be androgynous, and ever changing.”

Although Cheung quit his career as a pop singer from 1989 to 1995, he continued his music career as a songwriter. He composed more than ten songs during that time. In 1993, he won Best Original Movie Song Award from Golden Horse Film Festival for the theme song Red Cheek, White Hair to the film The Bride with White Hair (as a film score composer). In 1995, he wrote all three theme songs for the film The Phantom Lover. As for songwriting, Cheung won four nominations for Best Original Movie Song Award at the Golden Horse Film Festival and Awards and two nominations for Best Original Film Song at the Hong Kong Film Awards. In 1998, he was a member of the jury at the 48th Berlin International Film Festival.

In 1995 Cheung signed a contract with Rock Records, returning to music as a singer. At the same year, he released his first post-“retirement” album, Beloved. Beloved achieved large market success with the award of IFPI Best Selling Album.

Cheung was a supporter of several charities concerning children’s welfare. He was a patron of the Children’s Cancer Foundation, a charity that cares for young children with cancer and their families. Cheung donated HK$1 million (US$128,000) in 1996 and launched five sets of RED cards to help raise funds for the Children’s Cancer Foundation.

He was the first Cantopop star to launch a charity fundraiser at a concert. In 1996, although he rarely sang in public at that time, he sang three theme songs from his films to raise money for the elderly.

He announced his same-sex relationship with his childhood friend Daffy Tong Hok-tak (唐鶴德) during a concert in 1997, earning him prestige in LGBT communities in China, Japan, Taiwan, and Hong Kong. His relationship with Daffy lasted for almost 20 years until his death in 2003.

For his 1997 concert at the HK Coliseum, Cheung set up a collection booth for the RED Card charity. Donations of HK$100 or above could obtain a set of cards. Cheung said, “I will lead the way, so I donated HK$1,000,000 to Hong Kong children’s cancer fund in my own name.” The concert raised more than HK$800,000, to which Cheung and his friends added more than HK$100,000, and made up a million Hong Kong dollars to donate to the cancer fund.

In 1999, at a party to raise relief funds in the aftermath of the Taiwan earthquake, Cheung participated in a fried rice tasting event. He donated HK$250,000 for a bowl of rice; this was matched by fan donations, bringing the total to HK$500,000.

In 1999 and 2000, he appeared in TVB charity shows to help raise funds for ECSAF, in which he was appointed a goodwill ambassador in 2002.

Cheung responded to questions regarding his love life: “In terms of lovers, I think I can be a better friend than a lover. Because I am a workaholic. To share my romance, that person has to compromise something.” This statement was out during the interview following the release of the film Okinawa Rendez-vous in 2000.

In 2000, Sun Entertainment opened the “Star Second-hand Shop”, where second-hand goods donated by celebrities were auctioned to raise money for the “Sun Love Fund”. Leslie Cheung was known for his very good taste, and he was the first to donate three well-loved, carefully selected pieces to the auction. Leslie also donated his beloved badminton racket to IDclub Taiwan, to be auctioned to raise money for the children’s cancer fund.

In 2001 Cheung collaborated with William Chang, the art director of Wong Kar-Wai’s Days of Being Wild (1991), to make his music video Bewildered, about the intimacy between two gay men. Japanese ballet dancer Nishijima Kazuhiro played Cheung’s lover in the video. The music video was demonized for advocating homosexuality and was banned by TVB, but Cheung refused to edit the scenes and censor himself.

In a 2001 interview with Time magazine, Cheung said: “It’s more appropriate to say I’m bisexual. I’ve had girlfriends. When I was 22 or so, I asked my girlfriend Teresa Mo to marry me.”

As one of the most popular performers in Asia, Cheung’s death broke the hearts of millions of his fans across Asia and shocked the Asian entertainment industry and Chinese community worldwide. The day after Cheung’s death, his partner Daffy Tong confirmed that Cheung suffered from clinical depression and had been seeing Professor Felice Lieh Mak, a famous therapist, for treatment for almost a year. He also revealed that Cheung had previously attempted suicide in November 2002. Later at his funeral, Cheung’s niece disclosed that her uncle had severe clinical depression and suffered much over the past year. He was cremated & his ashes were buried in Po Fook Hill, Shatin.

In 2003, Cheung donated HK$100,000 to the Seedling protection fund, who were holding a large-scale charity night on the 12th of March. He told his party guests to give him cash instead of presents, then he donated all of the money that he received to the fund.

Cheung died of suicide on 1 April 2003 at 6:43 pm (HKT). He leapt from the 24th floor of the Mandarin Oriental hotel, located in the Central district of Hong Kong Island. He left a suicide note saying that he had been suffering from depression. He was 46 years old.

Despite the risk of infection from SARS and the WHO’s warning on traveling to Hong Kong, tens of thousands attended Cheung’s memorial service, which was held for the public, on 7 April 2003, including celebrities and other fans, many from other parts of the world such as mainland China, Taiwan, Korea, Japan, Southeast Asia, the United States, and Canada. Cheung’s funeral was held on 8 April 2003. For almost a month, Cheung’s death dominated newspaper headlines in Hong Kong and his songs were constantly on the air. His final album, Everything Follows the Wind (一切隨風), was released three months after his death.

In 2011, CCTV commented the “Passion Tour” that from performance form, art concept, costume props and audience response, all represent the highest standard of Chinese concerts, no one has ever surpassed.

In a 2012 interview, Cheung’s eldest sister, Ophelia, stated Cheung was diagnosed with clinical depression caused by a chemical imbalance in the brain. She said that reporters were frequently found outside of her brother’s home which hampered his ability to get to his doctor’s facility. Thus, he would come over to her house to consult with his doctor. He would ask his sister, “Why am I depressed? I have money and so many people love me.” He was reluctant to take medication for his depression.

In 2013, Cheung’s former music agent Florence Chan organised two memorial concerts entitled Miss You Much Leslie on 31 March and 1 April for the 10th anniversary of Cheung’s death. Big names of the Hong Kong entertainment industry performed at the concert at Hong Kong Coliseum. In addition, in 2013, Cheung’s fans from around the world made two million orizuru cranes for the Guinness World Record as a tribute to the anniversary.

On 12 September 2016, on what would have been Cheung’s 60th birthday, over one thousand fans joined Florence Chan in the morning at Po Fook Hill Ancestral Hall (寶福山) for prayers. At night, Cheung’s fans club, Red Mission organised “Leslie Cheung 60th Red Hot Birthday Party” to commemorate Cheung. It was an outdoor birthday party at Central Harbourfront Event Space with a big LED screen projecting Cheung’s past video clips, concerts, songs and pictures. Eason Chan (陳奕迅) as a member of Red Mission joined the party singing one of Cheung’s song “4 season” (春夏秋冬) as a tribute to Cheung. In the same month, another fans club, United Leslie also celebrated the big day of this renowned star. United Leslie organised an exhibition and movie screening of Cheung’s two selected movies in PMQ, Central of Hong Kong.

In 2018, 55383 Cheungkwokwing was named in memory of Leslie Cheung. The main-belt asteroid was discovered by Bill Yeung at the Desert Eagle Observatory in 2001.