Winehouse's debut album, Frank, was released on 20 October 2003. Produced mainly by Salaam Remi, many songs were influenced by jazz and, apart from two covers, every song was co-written by Winehouse. The album received positive reviews with compliments over the "cool, critical gaze" in its lyrics and brought comparisons of her voice to Sarah Vaughan, Macy Gray and others. The album entered the upper levels of the UK album chart in 2004 when it was nominated for BRIT Awards in the categories of "British Female Solo Artist" and "British Urban Act". It went on to achieve platinum sales.Later in 2004 she won the Ivor Novello (songwriting) Award for Best Contemporary Song, alongside Salaam Remi, with her contribution to the first single, "Stronger Than Me".The album also made the short list for the 2004 Mercury Music Prize. In the same year she performed at the Glastonbury Festival, the V Festival, the Montreal International Jazz Festival (7 July 2004, at the Club Soda), and on the Jazzworld stage. After the release of the album, Winehouse commented that she was "only 80 percent behind [the] album" because of the inclusion by her record label of certain songs and mixes she disliked. Additional singles from the album were "Take the Box", "In My Bed"/"You Sent Me Flying" and "Pumps"/"Help Yourself".
In contrast to her jazz-influenced former album, Winehouse's focus shifted to the girl groups of the 1950s and 1960s. Winehouse hired New York singer Sharon Jones's longtime band, the Dap-Kings to back her up in the studio and on tour. In May 2006 Winehouse's demonstration tracks such as "You Know I'm No Good" and "Rehab" appeared on Mark Ronson's New York radio show on East Village Radio. These were some of the first new songs played on the radio after the release of "Pumps" and both were slated to appear on her second album. The 11-track album was produced entirely by Salaam Remi and Ronson, with the production credits being split between them. Ronson said in a 2010 interview that he liked working with Winehouse because she was blunt when she did not like his work. Promotion of Back to Black soon began and, in early October 2006 Winehouse's official website was relaunched with a new layout and clips of previously unreleased songs.Back to Black was released in the UK on 30 October 2006. It went to number one on the UK Albums Chart numerous times, and entered at number seven on the Billboard 200 in the US. It was the best-selling album in the UK of 2007, selling 1.85 million copies over the course of the year.
The album spawned a number of singles. The first single released from the album was the Ronson-produced "Rehab". The song reached the top ten in the UK and the US.Time magazine named "Rehab" the Best Song of 2007. Writer Josh Tyrangiel praised Winehouse for her confidence, saying, "What she is is mouthy, funny, sultry, and quite possibly crazy" and "It's impossible not to be seduced by her originality. Combine it with production by Mark Ronson that references four decades worth of soul music without once ripping it off, and you've got the best song of 2007." The album's second single and lead single in the US, "You Know I'm No Good", was released in January 2007 with a remix featuring rap vocals by Ghostface Killah. It ultimately reached number 18 on the UK singles chart. The title track, "Back to Black", was released in the UK in April 2007 and peaked at number 25, but was more successful across mainland Europe."Tears Dry on Their Own", "Love Is a Losing Game" and "Just Friends" were also released as singles, but failed to achieve the same level of success.
A deluxe edition of Back to Black was also released on 5 November 2007 in the UK. The bonus disc features B-sides, rare, and live tracks, as well as "Valerie". Winehouse's debut DVD I Told You I Was Trouble: Live in London was released the same day in the UK and 13 November in the US. It includes a live set recorded at London's Shepherds Bush Empire and a 50-minute documentary charting the singer's career over the previous four years. Frank was released in the United States on 20 November 2007 to positive reviews.The album debuted at number 61 on the Billboard 200 chart.
In addition to her own album she collaborated with other artists on singles. Winehouse was a vocalist on the song "Valerie" on Ronson's solo album Version. The song peaked at number two in the UK, upon its October single release. The song was nominated for a 2008 Brit Award for "Best British Single".Her work with ex-Sugababe Mutya Buena, "B Boy Baby", was released on 17 December 2007. It served as the fourth single from Buena's solo debut album, Real Girl.