Richard’s “big break” came in 2005 when she auditioned for the MTV show Making the Band 3 in Orlando, where she was chosen to compete for a spot in Combs’ future girl group. After the negotiated release from her contract with Yeah! Brother Records, she elevated her career by signing with Bad Boy Worldwide Entertainment. She beat out numerous contestants to secure herself a spot, along with Aubrey O’Day, Aundrea Fimbres, Wanita Woodgett (now known as “D. Woods”), and Shannon Bex.

The newly formed group became Danity Kane. The idea for the name came from one of Richard’s drawings. An avid fan of manga, while Danity Kane was in the studio, Richard drew a female superhero which caught the attention of Combs. When asked what the character’s name was, she replied, “Danity Kane”. To Combs, this represented the girls of Making the Band 3. He then decided that it should be the name of the group. The name and story were first introduced during Danity Kane’s Total Request Live appearance on June 14, 2006.

Early in 2008, a song called “Phase” was leaked onto the Internet and featured Lil Wayne. Although it was buzzed as a Danity Kane track, only Richard’s voice was featured on the song, which caused speculation that it was a solo demo. In July 2008, two new tracks were released onto the internet, one called “Rush Love” which featured Flo Rida, and another called “Strobe Light”, written by Mary Brown and produced by Chad Beatz (Tastemaker Music). It is still unknown if this was part of a future solo endeavor.

During an MTV News break, it was stated that Richard was working on an untitled comic book. Richard also said in an interview that she would be releasing a soundtrack for the Danity Kane comic book, to be released in March 2009. Included would be the leaked track “Falls Away”.

On January 27, 2009, Richard confirmed to MTV News in an interview that Danity Kane had completely split up. In the same interview, she said that she still considered herself a member of Danity Kane (along with Aundrea Fimbres), and had hopes that each girl would be willing to work as a group again.

In 2009, Richard began working with Bad Boy Records, writing for artist Cassie and Combs himself. Soon after Danity Kane’s breakup, Richard was featured in a commercial for the opposition of California’s Prop 8. Richard became a member of the Diddy-Dirty Money collective, which includes Combs and singer-songwriter Kalenna Harper. She featured in Keri Hilson’s video for “The Way You Love Me” as “Money”. She is the first member of Danity Kane to have released professional music under a major label after their split, with the Dirty Money album.

During 2010, Richard started putting the finishing touches on her mixtape, The Prelude to A Tell Tale Heart. Before the full mix-tape release Richard released a few songs, including “Me Myself & Y”, which she released as a promotional single on globalgrind.com. Others are “These Tears”, a heavy ballad, and “Let Love In”, another ballad with heavy vocal harmonies. The mixtape The Prelude to A Tell Tale Heart (alternate title: #ATellTaleHeart) was released on February 7, 2011 on her official website. It contains 15 tracks. It was called “the prelude to…” because there will also be an official debut studio album by Dawn Richard entitled A-Tell Tale Heart, which she has been working on for three years. She worked with Trendsetter (the producer) on a few tracks for that album.

On June 19, 2011 a buzz track entitled “Stuck on Mad” was released to the public. followed by a release of a remix to Frank Ocean’s “Novacane”. The remix, which was co-written by songwriter Intyce, hit the internet on June 21, 2011 and reached over 5,000 downloads within a few hours.

Dawn released the visual for her first promotional single “SMFU (Save Me From U)” on 106 & Park in January 2012. Other promotional singles such as “Fly, Change, and Black Lipstick” came after. She quickly followed with a leading single titled “Bombs”. The video has been compared to Beyonce’s “Run The World (Girls)” and Nicki Minaj’s “Massive Attack”. The video shows heavy choreography in a desert. After the success of “Bombs”, Richard’s next official single from Armor On was released: “Automatic”, the most urban track from the EP. The video was released on June 18 and premiered on 106 & Park. The following music video was filmed in July 2012. Richard released three video trailers on YouTube for her singles “Faith” and “Wild N’Young”, which were meshed into one music video released on August 29, 2012 as the final release from Armor On.

Richard announced that her major solo debut project will be a trilogy of albums entitled Goldenheart, BlackHeart, and RedemptionHeart. GoldenHeart was expected to be released on October 16, 2012. “SMFU (Save Me from U)” was released on the internet on October 31, 2011, and will on the first album. The video premiered on 106 & Park on January 5, 2012. Druski is the main producer on this entire project.

In celebration of her one million Twitter followers, Richard introduced the set-up for her album GoldenHeart on July 17, 2012 with a track entitled “Pretty Wicked Things”. “It’s the story of the beautiful things in life that get ruined by the wicked,” explained Richard. It was produced and co-written by Armor On collaborator Druski, and is available on iTunes.

Goldenheart was released on January 15, 2013 in stores and through online retailers. Originally intended for release in October 2012, Richard delayed the release after signing a distribution deal with independent company Altavoz Distribution, which would release physical copies to retailers, and provide a wider marketing reach. The album’s lead single, “’86”, was released as a digital download on September 26.

Goldenheart was released in the United States on January 15, 2013. Richard released the album independently, as she felt record labels were “taking a bit longer than we want”. It debuted at number 137 on the Billboard 200, number 2 on the Top Heatseekers Albums, and number 10 on the Top R&B/Hip-Hop Albums. The album also reached the top of the iTunes Store’s R&B chart, which prompted music retailer f.y.e. to preemptively release its physical CD.

Richard was scheduled to release the second installment in her album trilogy, BlackHeart, in October 2013, but announced that the album would be released after the Danity Kane project. On New Year’s Day of 2014, the unreleased music video for “Riot/Northern Lights” was leaked online. The video was originally shelved in May 2013 after Richard and producer Drew Scott parted ways. The video received positive reviews as it continued where the “86” music video left off.

During the 2013 MTV VMAs pre-show, the four remaining members of Danity Kane announced that they were reuniting and returning on their own terms, without Diddy. Original group member D. Woods did not take part in the reunion. The group’s first official reunion single, “Lemonade”, was released on the Internet via SoundCloud. The single was produced by the Stereotypes, and features rapper Tyga over a production sampled from “Grindin'”, the 2002 hit song by Clipse.

In 2013 Richard partnered with Coco & Breezy to release her own line of sunglasses to accompany her debut album. In 2014 she launched a capsule collection of women’s shoes via Lust for Life, and a new addition of shades to accompany the Blackheart album release. In 2016 Richard released a limited edition sterling silver and red USB necklace to accompany the trilogy finale REDEMPTION.

On May 16, 2014, the first night of their #DKNoFilter Tour after performing several songs with Danity Kane, Fimbres announced that she would be leaving the group at the end of their tour, and that O’Day, Bex, and Richard would be continuing on as a trio.

On August 4, 2014 while in a Los Angeles recording studio, a fight ensued in which Richard allegedly punched O’Day. After days of speculation, O’Day and Bex released a public statement announcing the group’s second disbandment. Despite the group’s break-up, their third album, DK3, was released on October 27, 2014.

On October 29, 2014, two days after DK3’s release, Richard debuted the music video for her lead single “Blow” to Vevo. Along with the video, she announced the new release date for her second album Blackheart, January 15, 2015.

On September 28, 2015, Richard debuted “Dance”, the first single from The Red Era. About the single she said: “I wanted to create a vibrant atmosphere, The Red Era is about moving on, redeeming yourself, and finding redemption. The official music video premiered on October 5, 2015, mashed with “Billie Jean” from Blackheart.

On January 29, 2016 “Not Above That” was released through UK label Local Action. On March 12, 2016 Dawn started her Redemption Live show tour and performed the first ever YouTube live 360 performance.

On August 10, 2016 Richard made a cameo appearance on Season 2 of the TV series Rosewood with Morris Chestnut and Gabrielle Dennis.

On September 15, 2016, Richard began filming the lead role, Joyce, in the 2017 movie Kinky, written by Jean-Claude Lamarre and starring Robert Ri’chard, Gary Dourdan and Vivica A. Fox.

On November 10, 2016, Redemption was made available to stream exclusively on NPR one week ahead of its release. The album was officially released on November 18, 2016.

On January 25, 2019 Richard released her 5th solo album, New Breed. On September 7, 2020, Dawn was cast in the limited series Trace alongside actor Gary Leroi Gray. Also in September 2020, according to Deadline Hollywood, Richard joined the cast of the Indie thriller Issac alongside Dove Cameron and RJ Mitte.