On 10 February 2008, Winehouse received five Grammy Awards, winning in the following categories: Record of the Year, Song of the Year, Best Female Pop Vocal Performance for the single "Rehab," and Best Pop Vocal Album. The singer also earned a Grammy as Best New Artist, earning her an entry in the 2009 edition of the Guinness Book of Records for Most Grammy Awards won by a British Female Act. Additionally, Back to Black was nominated for Album of the Year. Ronson's work with her won the Grammy Award for Producer of the Year, in the non-classical category. She ended her acceptance speech for Record of the Year with, "This is for London because Camden town ain't burning down," in reference to the 2008 Camden Market fire. Performing "You Know I'm No Good" and "Rehab" via satellite from London's Riverside Studios at 3 a.m. UK time, she couldn't be at the ceremony in Los Angeles as her visa approval had not been processed in time.
After the Grammys, the album's sales increased, catapulting Back to Black to number two on the US Billboard 200, after it initially peaked in the seventh position. On 20 February 2008, Winehouse performed at the 2008 Brit Awards at Earls Court in London, performing "Valerie" with Mark Ronson, followed by "Love Is a Losing Game." She urged the crowd to "make some noise for my Blake." A special deluxe edition of Back to Black topped the UK album charts on 2 March 2008. Meanwhile, the original edition of the album was ranked at number 30 in its 68th week on the charts, while Frank charted at number 35.
In Paris, she performed what was described as a "well-executed 40-minute" set at the opening of a Fendi boutique in early March. By 12 March, the album had sold a total of 2,467,575 copies—318,350 copies had been sold in the previous 10 weeks—putting the album on the UK's top-10 best-selling albums of the 21st century for the first time. On 7 April, Back to Black was in the top position of the pan-European charts for the sixth consecutive and thirteenth aggregate week. Amy Winehouse – The Girl Done Good: A Documentary Review, a 78-minute DVD, was released on 14 April 2008. The documentary features interviews with those who knew her at a young age, people who helped her achieve success, jazz music experts, and music and pop-culture specialists.
At the 2008 Ivor Novello Awards in May, Winehouse became the first-ever artist to receive two nominations for the top award: Best Song Musically & Lyrically. She won the award for "Love Is a Losing Game" and was nominated for "You Know I'm No Good." "Rehab," a Novello winner for best contemporary song in 2006, also received a 2008 nomination for best-selling British song. Winehouse was also nominated for a 2008 MTV Europe Award in the "Act of the Year" category.
Although her father, manager and various members of her touring team reportedly tried to dissuade her, Winehouse performed at the Rock in Rio Lisboa festival in Portugal in May 2008. Although the set was plagued by a late arrival and problems with her voice, the crowd warmed to her. In addition to her own material she performed two Specials covers. Winehouse performed at Nelson Mandela's 90th Birthday Party concert at London's Hyde Park on 27 June 2008, and the next day at the Glastonbury Festival. On 12 July, at the Oxegen Festival in Ireland she performed a well-received 50-minute set which was followed the next day by a 14-song set at T in the Park.
A clip of Winehouse's music was included in the "Roots and Influences" area that looked at connections between different artists at the Rock and Roll Hall of Fame Annex NYC, which opened in December 2008. One thread started with Billie Holiday, continued with Aretha Franklin and Mary J. Blige, and then finished with Winehouse.
Winehouse joined a campaign to stop a block of flats being built beside the George Tavern, a famous London East End music venue. Campaign supporters feared the residential development would end the spot's lucrative sideline as a film and photo location, on which it relies to survive. As part of a breast cancer awareness campaign, Winehouse appeared in a revealing photograph for the April 2008 issue of Easy Living magazine. Winehouse had an estimated £10m fortune, tying her for tenth place in the 2008 The Sunday Times listing of the wealth of musicians under age 30. The following year her fortune had dropped to an estimated £5m. Her finances are run by Mitch and Janis Winehouse. It was reported she earned about £1m singing at two private parties during Paris Fashion Week. as well as another £1m to perform at a Moscow Art Gallery for Russian oligarch Roman Abramovich. Winehouse loaned a vintage dress used in her video for "Tears Dry on Their Own" as well as a DVD to the British Music Experience, a new museum dedicated to the history of British pop music. The museum, located at the O2 Arena in London, opened on 9 March 2009.
Winehouse's use of bold red lipstick, thick eyebrows and heavy eyeliner came from Latinas she saw in Miami, on her trip there to work with Salaam Remi on Back to Black. Her look was repeatedly denigrated by the British press. At the same time that the NME Awards nominated Winehouse in the categories of "Best Solo Artist" and "Best Music DVD" in 2008, they awarded her "Worst Dressed Performer." Winehouse was also ranked number two on Richard Blackwell's 48th annual "Ten Worst Dressed Women" list, behind Victoria Beckham.
By 2008, her drug problems threatened her career. As Nick Gatfield, the president of Island Records, toyed with the idea of releasing Winehouse "to deal with her problems", he said, "It's a reflection of her status [in the US] that when you flick through the TV coverage [of the Grammys] it's her image they use." Post-Grammys, some questioned whether Winehouse should have been honoured with the awards given her recent personal and drug problems, including Natalie Cole, who introduced Winehouse at the ceremony and who herself battled substance-abuse problems while winning a Grammy for Best New Artist in 1975. (Winehouse was prevented from travelling to and performing at the Grammy Awards ceremony in the US due to failing a drug test.) In a newspaper commentary, the executive director of the UN Office on Drugs and Crime, Antonio Maria Costa, said that the alleged drug habits of Winehouse and other celebrities sent a bad message "to others who are vulnerable to addiction" and undermine the efforts of other celebrities trying to raise awareness of problems in Africa, now that more cocaine used in Europe passes through that continent. Winehouse's spokesperson noted that "Amy has never given a quote about drugs or flaunted it in any way. She's had some problems and is trying to get better. The U.N. should get its own house in order."
In January 2008, her record label stated it believed the extensive media coverage she had received increased record sales. In an April 2008 poll conducted by Sky News, Winehouse was named the second greatest "ultimate heroine" by the UK population at large, topping the voting for that category of those polled under 25 years old. Psychologist Donna Dawson commented that the results demonstrated that women like Winehouse who had "a certain sense of vulnerability or have had to fight against some adversity in their lives" received recognition.
In July 2008, BBC Radio Scotland's head, Jeff Zycinski, stated that the BBC, and media in general, were complicit in undermining celebrities, including Winehouse. He said that public interest in the singer's lifestyle did not make her lifestyle newsworthy. Rod McKenzie, editor of the BBC Radio One programme Newsbeat, replied: "If you play [Amy Winehouse's] music to a certain demographic, those same people want to know what's happening in her private life. If you don't cover it, you're insulting young licence fee payers." In The Scotsman, British singer and songwriter Lily Allen was quoted to have said – "I know Amy Winehouse very well. And she is very different to what people portray her as being. Yes, she does get out of her mind on drugs sometimes, but she is also a very clever, intelligent, witty, funny person who can hold it together. You just don't see that side."
In 2008, Winehouse appeared naked in an issue of Easy Living Magazine to raise awareness of breast cancer. In 2009, she appeared on a CD called Classics alongside musicians such as the Rolling Stones, the Killers and many Cuban musicians to raise awareness of climate change. In March 2011, Winehouse donated over £20,000 worth of clothes to a local charity shop in London.
London's Mall Galleries opened an exhibition in May 2008 that included a sculpture of Winehouse, titled Excess. The piece, created by Guy Portelli, had a miniature of the singer lying on top of a cracked champagne bottle, with a pool of spilled liquid underneath. The body was covered with what appeared to be tiny pills, while one outstretched hand held a glass. Another piece, a print titled Celebrity 1 by artist Charlotte Suckling, was shown in the same exhibition.
A wax sculpture of Winehouse went on display at the London Madame Tussauds on 23 July 2008. The singer did not attend the unveiling, although her parents did. A sculpture by Marco Perego, titled The Only Good Rock Star Is a Dead Rock Star, that depicts Winehouse lying in a pool of blood with an apple and a bullet hole in her head after being shot by American novelist and Beat poet William S. Burroughs (in a recreation of the accidental killing of his wife Joan Vollmer), was scheduled to go on display in New York's Half Gallery on 14 November 2008 with a sale price of US$100,000. Perego said of the sculpture: "Rock stars are the sacrificial animals of society." Winehouse's spokesperson stated: "It's a funny kind of tribute. The artist seems in thrall to a tabloid persona that is not the real Amy. People often use her image to sell their work."
After Winehouse's death, Pete Doherty said that he and Winehouse had been lovers at one point. However, in July 2008, when Rolling Stone reporter Claire Hoffman asked Winehouse about her relationship with Doherty, Winehouse replied: "We're just good friends", and added: "I asked Pete to do a concept EP, and he made this face, he looked at me like I'd pooed on the floor. He wouldn't do it. We're just really close".
On 23 January 2008, the video was passed on to the Metropolitan Police, who questioned her on 5 February. No charges were brought. On 26 March 2008, Winehouse's spokesman said she was "doing well". Her record company reportedly believed that her recovery remained fragile. By late April 2008, her erratic behaviour—including an allegation of assault—caused fear that her drug rehabilitation efforts had been unsuccessful. Winehouse's father and manager then sought to have her detained under the Mental Health Act of 1983. Her dishevelled appearance during and after a scheduled club night in September 2008 sparked new rumours of a relapse. Photographers were quoted as saying she appeared to have cuts on her legs and arms.
According to her physician, Winehouse quit using illegal substances in 2008. In an October 2010 interview, speaking of her decision to quit drugs, Winehouse said, "I literally woke up one day and was like, 'I don't want to do this any more.'" However, alcohol emerged as a problem, with Winehouse abstaining for a few weeks and then lapsing into alcohol abuse. Her physician said that Winehouse was treated with Librium for alcohol withdrawal and anxiety and underwent psychological and psychiatric evaluations in 2010, but refused psychological therapy.
On 26 April 2008, Winehouse was cautioned after she admitted to police she slapped a 38-year-old man in the face, a "common assault" offence, her first of two. She voluntarily turned herself in and was held overnight. Police said, at her arrival she was "in no fit state" to be interviewed. Ten days later, Winehouse was arrested on suspicion of possessing drugs after a video of her apparently smoking crack cocaine was passed to the police in January, but was released on bail a few hours later because they could not confirm, from the video, what she was smoking. The Crown Prosecution Service considered charging her, but cleared her when it could not establish that the substance in the video was a controlled drug. Some members of Parliament reacted negatively. Two London residents were subsequently charged with conspiracy to supply cocaine and ecstasy to Winehouse. One of the pair was sentenced to two years in prison on 13 December 2008, while the other received a two-year community order.
On 23 June 2008, Winehouse's publicist corrected earlier misstatements by Mitch Winehouse that his daughter had early stage emphysema, instead claiming she had signs of what could lead to early-stage emphysema. Mitch Winehouse had also stated that his daughter's lungs were operating at 70 percent capacity and that she had an irregular heartbeat. He said that these problems had been caused by her chain smoking crack cocaine. The singer's father also reported that doctors had warned Winehouse that, if she continued smoking crack cocaine, she would have to wear an oxygen mask and would eventually die. In a radio interview, Mitch Winehouse said the singer was responding "fabulously" to treatment, which included being covered with nicotine patches. British Lung Foundation spokesman Keith Prowse noted this type of condition could be managed with treatment. Prowse also said the condition was not normal for a person her age but "heavy smoking and inhaling other substances like drugs can age the lungs prematurely." Norman H. Edelman of the American Lung Association explained that if she stopped smoking, her lung functions would decline at the rate of a normal person, but continued smoking would lead to a more rapid decline in lung function.
Winehouse was released from the London Clinic 24 hours after returning from a temporary leave to perform at Nelson Mandela's 90th birthday and at a concert in Glastonbury, and continued receiving treatment as an outpatient. In July 2008, Winehouse stated that she had been diagnosed with "some areas of emphysema" and said she was getting herself together by "eating loads of healthy food, sleeping loads, playing my guitar, making music and writing letters to my husband every day." She also kept a vertical tanning bed in her flat. Winehouse began precautionary testing on her lungs and chest on 25 October 2008 at the London Clinic for what was reported as a chest infection. Winehouse was in and out of the facility and was granted permission to set her own schedule regarding home leave. She returned to the hospital on 23 November 2008 for a reported reaction to her medication.