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In 2014, she released her first commercial mixtape, Cloud 19. The mixtape was listed as one of the Complex' s "50 Best Albums of 2014." Her second commercial mixtape, You Should Be Here (2015), debuted at number 5 on the R&B/Hip-Hop chart, preceded by her sold-out North American promotional tour. In 2016, she was nominated for the Grammy Award for Best Urban Contemporary Album for You Should Be Here. Kehlani released her debut studio album, SweetSexySavage, in January 2017. She released her second studio album It Was Good Until It Wasn't on May 8, 2020.

In 2019, Kehlani was featured on Russian-German DJ Zedd's single "Good Thing" and American singer Teyana Taylor's single "Morning", respectively. In January 2020, Kehlani was featured on Canadian singer Justin Bieber's song "Get Me" from his fifth studio album, Changes. Kehlani released her second studio studio album It Was Good Until It Wasn't on May 8, 2020.

On February 22, 2019, her third commercial mixtape While We Wait was released by Atlantic Records and debuted at number nine on the US Billboard 200. The mixtape had 34,000 album-equivalent units including 6,000 pure sales in its first week. It is supported by singles, "Nights Like This" featuring Ty Dolla Sign, "Nunya" featuring Dom Kennedy, and "Butterfly".

On September 6, 2019, it was confirmed that Kehlani was dating West coast rapper YG., but after three months of dating, Kehlani and YG broke up. However, the two released a collaborative single for Valentine's Day, "Konclusions", on February 14, 2020. In May 2020, during an interview with The Breakfast Club, Kehlani said she discovered that YG was cheating on her after seeing his phone, explaining "I've seen his phone and there just was things that I just didn't need to see that were not surface level things". YG apologized by filling her lawn with roses. Kehlani added that they do not speak, but remain cordial.

Kehlani served as an opening act on American singer Demi Lovato's Tell Me You Love Me World Tour in North America, which started on February 26, 2018 and concluded on April 2, 2018. In March 2018, Kehlani was featured on American singer Charlie Puth's single "Done for Me", from his second studio album, Voicenotes. In April 2018, she was featured on American rapper Cardi B's single "Ring", from her debut studio album, Invasion of Privacy The song entered at number 28 on the Billboard Hot 100, making Kehlani's first top 40 entry on the chart. Kehlani is currently represented by David Ali of Above Ground Management. She then opened on American singer Halsey's Hopeless Fountain Kingdom World Tour in Oceania, which started on April 19, 2018.

Kehlani has publicly identified as queer and pansexual. In 2018, she clarified her sexuality on Twitter, stating, "I'm queer. Not bi, not straight. I'm attracted to women, men, REALLY attracted to queer men, non-binary people, intersex people, trans people. lil poly pansexual". After she recuperated, in 2017, she had multiple posts about love for everyone regardless of gender identity, and was motivating fans to accept people's differences and beliefs. While on the SweetSexySavage World Tour, she posted pictures of her girlfriend, New Jersey artist Shaina Negron. In April 2018, Kehlani posted on Twitter that she identified with the term queer over gay because gay "always insisted there was still a line drawn as to which 'label' of human i was attracted."

Kehlani announced that she was pregnant with her first child, a girl, on Instagram on October 12, 2018, with the father being Javaughn Young-White, who is her guitarist and the brother of comedian Jaboukie Young-White. She opened up in December 2018 about prenatal depression and how her pregnancy is harder than it might look. On March 23, 2019, Kehlani gave birth to her daughter, Adeya Nomi Parrish YoungWhite at home. "Home-birth is a medical decision as is hospital birth, all birth is mind blowing & powerful. [Using] my experience to shame another's isn't what I want, power to anyone who brings life forth, it’s a next level journey whichever way."

On January 5, 2018, Kehlani posted a photo to Instagram showing that her "woke" hand tattoo had been now covered up with a lotus flower; she stated that she felt that her "hand would speak for [her] before [she] even got a chance to open [her] mouth".

On her travels to Australia during August 2017, Kehlani received a New Zealand Maori "Tāmoko" tattoo from a New Zealand artist, whom she flew from New Zealand to Sydney, Australia to complete the tattoo. On Kehlani's Instagram post, she captioned the photo: "[T]he piece representing my whānau/family, 6 koru representing my 4 siblings here on earth and the 2 that have transferred into the next life. 2 mangopare/hammerhead sharks representing guidance and strength through adversity and tribulation."

On November 26, 2016, Kehlani revealed the title of her debut studio album SweetSexySavage, which was released on Atlantic Records on January 27, 2017. In December 2017, Kehlani was featured on American rapper Eminem's single "Nowhere Fast", from his ninth studio album Revival. Kehlani's third annual Tsunami Christmas tour concluded in Santa Ana, California on December 18, 2017.

In January 2016, it was confirmed that Kehlani was in a relationship with star NBA point guard Kyrie Irving. In March 2016, Canadian musician PartyNextDoor posted a picture of Kehlani's hand on Instagram insinuating that they were in bed together. This caused a media controversy across Twitter, in which abuse was tweeted against Kehlani in hundreds of thousands of posts. Irving would tweet that they had broken up before the incident. Kehlani took to social media to explain that she did not cheat on Irving, saying, "No one was cheated on and I'm not a bad person..." in what was also a public statement to acknowledge her attempted suicide in the wake of the media attention. In 2018, Irving would pen an apology to Kehlani via an Instagram post, expressing appreciation towards the singer, in which he described himself as "grateful" to know her. Kehlani responded, also on Instagram, saying, "I appreciated it no matter how long it took, i respect it being done period when really neither of us should be the one apologizing."

On April 28, 2015, she released her second mixtape You Should Be Here. Billboard called it the "year's first great R&B album", when it debuted at number 5 on the US Billboard's Top R&B/Hip-Hop Albums. The project features guest appearances from fellow American rapper Chance the Rapper and American singer BJ the Chicago Kid. A week after the release, she announced that she had signed a deal to Atlantic Records. In support of the Mixtape, she went on the You Should Be Here tour, which sold out every North American date and select European dates. Throughout 2015, she also received individual plaudits: Complex called her one of the "15 Artists to Watch Out for in 2015" and Rolling Stone named her one of the "10 New Artists You Need to Know." She was also nominated for a 2016 Grammy Award for Best Urban Contemporary Album. In March 2016, Kehlani was featured on English singer and friend Zayn on his single, "Wrong" from his debut solo studio album Mind of Mine. Her song "Gangsta" was featured on the soundtrack for the August 2016 hit movie Suicide Squad, which gave her and her music some beneficial recognition, as it reached number 41 on the Hot 100.

In 2014, the studio time culminated in the release of her first mixtape, called Cloud 19. The mixtape features guest appearances from Kyle Dion. Cannon also sent her to New York City to work with record producer Jahaan Sweet. The mixtape ranked at twenty-eighth on Complex's list of the "50 Best Albums of 2014," and was also listed among Pitchfork's "Overlooked Mixtape's 2014." A song she released in late 2014, "Till the Morning" was placed by Billboard as one of the "Emerging Picks of the Week" on November 7, 2014. In 2015, Kehlani opened for American rapper G-Eazy on the second leg of his From the Bay to the Universe tour.

After the end of America's Got Talent, Kehlani left PopLyfe, because of several managerial and contractual disputes. Over six months, she avoided doing anything music related to avoid being sued by the group's management. In 2012 and 2013, Kehlani was effectively homeless, moving from house to house and often sleeping on couches. During her senior year of high school, she moved to Los Angeles, California, with no legal guardian. In 2013, Nick Cannon, who had been the host of America's Got Talent during PopLyfe's run, called Kehlani to ask her about being in a rap group. She agreed at first and went to Los Angeles, but, ultimately didn't like the direction of the group and moved back to Oakland. To help with money and food, she decided to begin stealing iPhones to sell, and items from grocery stores for a short time. Months later, Kehlani released her first solo track on SoundCloud, called "ANTISUMMERLUV". Cannon called her back after hearing the song and he bought her an apartment in LA, along with studio time.

Kehlani's singing career effectively began when she started out as a member and lead vocalist for the group called PopLyfe. The band's music was produced by former Tony! Toni! Tone! member D'Wayne Wiggins. Within two years, the group performed throughout the Bay Area and other cities. In 2011, they auditioned for the sixth season of America's Got Talent, and eventually finished in fourth place. During their final appearance, judge Piers Morgan told Kehlani, "You've got real talent, but I don't think you need the group."

Kehlani Ashley Parrish (born April 24, 1995) is an American singer, songwriter, and dancer. Kehlani is originally from Oakland, California, where she achieved initial fame as a member of the teen group Poplyfe.

Kehlani Ashley Parrish was born on April 24, 1995, in Oakland, California. She has described her ethnicity as a mix of "Black, White, Native American and Mexican." Her father was African-American and her mother has been described as "mostly White". She was adopted and raised by her aunt when her mother, who had a drug addiction, served time in prison. Kehlani's father, who also had a drug addiction, died when she was a toddler. During her teenage years, she attended the Oakland School for the Arts, where she initially practiced dance, particularly ballet and modern dance.