Son Dam-bi first came to fame when she appeared in a commercial for an MP3 player alongside Poppin' Hyun Joon. Before her debut, MSN Japan made a video documentary capturing her pre-debut training and rehearsals; it attracted 480,000 visitors in 5 days. Son Dam-bi trained with a well-known American choreographer in preparation for this album, and people began calling her the female version of Rain (비).
Son Dam-bi’s debut single features five tracks that show off her vocal and dancing talents. Her debut single "Cry Eye" was produced and composed by Jang Joon Ho, who previously wrote MC Mong's "180 Degrees" and Jang Woo Hyuk's "Last Game". The lyrics were provided by Brian Kim, who also penned Shinhwa’s Once in A Lifetime.
Son Dam-bi joined MBC's reality show 우리 결혼했어요 ("We Got Married"), being paired with Marco. Joining the show in late 2008 as part of the second group of couples, their last episode was on February 2, 2009.
It was also announced that Son would be part of the cast for Hype Nation, a film that has been labelled a "world movie". However, as the movie was delayed, Son released a mini-album with the single "Toyoil Bamae" ("토요일 밤에", "On a Saturday Night"). The song became her first #1 hit, topping various on- and offline charts, including M! Countdown (within 20 days), two wins on KBS's Music Bank, a 3-week chart-topping run on SBS's Inkigayo. The song's routine features Son in various 80s fashions, transforming her into a "retro fashionista".
After training in the United States after "Cry Eye", Son Dam-bi returned to Korea and released a mini album, Mini Album Vol.1, with a focus on electronica (departing from her previous style of crunk pop) on April 29, 2008. The lead title was "Bad Boy", produced by Brave Brothers. Also, Kahi (former leader of After School and Pledis labelmate) was her dance teacher, and was featured in the Bad Boy music video.
Her follow-up song in 2009, "Toyoilbamae" (Korean: "토요일밤에", "On a Saturday Night"), was a success. She then released her next EP, The Queen.
2011–present: "Lights and Shadows" and "Dripping Tears" comeback
Starting in 2011, Son Dam-bi starred in a drama called Lights and Shadows. It was first broadcast on November 28, 2011. She finished filming in June 2012 with the drama concluding on July 3, 2012. She also released an OST for the drama called "Everything" on January 10, 2012.
It was confirmed by Pledis Entertainment that Son Dam-bi would make a comeback in Korea sometime in the summer. Eventually, a representative from Pledis stated that Dam-bi was finished recording her album and was in the midst of shooting photos for the album jacket. It was eventually confirmed that Son Dam-bi's new comeback album would be released sometime in early August. However, Pledis then stated that they would push Dam-bi's comeback even further into the year. It was then confirmed that Son Dam-bi will be coming back with the fourth mini album and it was released on November 12, 2012. The title track, "Dripping Tears," is produced by Brave Brothers. The fourth mini album titled "Dripping Tears," same with the title track and it contained 6 songs, included a 'G. Remix version' of "Dripping Tears." The music video of "Dripping Tears" released a day after the album. She had her first comeback in almost 2 years on November 15 on 'M Countdown.'