Question: Which Canadian singer began his recording career with a self-titled debut album released on May 19 1998, and won Rolling Stone's Best New Artist award that year?

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MTV Video Music Award for Best New Artist: The MTV Video Music Award for Best New Artist have been given out since the first annual MTV Video Music Awards in 1984.  From then to 2006, the award was named Best New Artist in a Video.  In 2007 its name was changed to Best New Artist, as the category underwent a format change to award the artist's body of work for the full year rather than a specific video.  For the 2008 ceremony, though, while the award retained its 2007 name, it returned to the format of awarding a specific video rather than the artist's full body of work.  The category was later renamed Artist to Watch through 2013 to 2015 while still keeping the format of an award going to a certain video.

Grammy Award for Best New Artist: The Grammy Award for Best New Artist has been awarded since 1959.  Years reflect the year in which the Grammy Awards were handed out, for records released in the previous year.  The award was not presented in 1967.  The official guidelines are as follows: "For a new artist who releases, during the Eligibility Year, the first recording which establishes the public identity of that artist."  Note that this is not necessarily the first album released by an artist.

Amy Holland (album): Amy Holland is singer Amy Holland's self-titled debut album.  The album was released on LP record in 1980, and was produced by Amy's future husband Michael McDonald.  One of the songs on the album "How Do I Survive" (a song originally sung by The Paul Bliss Band) became a big hit and made it to the Top 30 chart.  Amy Holland would often perform "How Do I Survive" live on music TV shows such as Music Fair (a Japanese music show) and Young Oh!  Oh! .  Those live performances of the song can be found on YouTube.  Holland mostly recorded some song covers for this album, with one of them being Annette Hanshaw's 1928 jazz-standard "Forgetting You" The success of the song "How Do I Survive" helped Amy earn a Grammy Nomination for Best New Artist in 1981, but she did not win the award however.  Some of the songs on the album have been written by Michael McDonald such as "Here In The Light" and "Show Me the Way Home".  "How Do I Survive" was a hit peaking at #22 on the "Billboard" Hot 100.  Three years later Amy would release another studio album called "On Your Every Word".

Rufus Wainwright discography: The discography of Rufus Wainwright, a Canadian-American singer-songwriter, consists of seven studio albums, three live albums, three compilations, three extended plays (EPs), three video albums, nine singles, and nine music videos. Wainwright's self-titled debut album was released through DreamWorks Records in May 1998.  Although his success was limited, Wainwright reached #24 on "Billboard's" Top Heatseekers chart, and "Rolling Stone" named him 1998's Best New Artist.  Wainwright's second album, "Poses", was released through the same label in June 2001, resulting in the #1 position on the Heatseekers Chart and #117 on the "Billboard" 200.  With material recorded from the same session, "Want One" was released through DreamWorks in September 2003, and "Want Two" was released through Geffen Records in November 2004.

Sailing (Christopher Cross song): "Sailing" is a song written and recorded by American artist Christopher Cross.  It was released in June 1980 as the second single from his eponymous debut album.  The song was a success in the USA, winning Grammy Awards for Record of the Year, Song of the Year, and Arrangement of the Year, and helping Cross win the Best New Artist award.  VH1 named this the greatest "softsational soft rock" song of all time.

Ana Bárbara (album): Ana Bárbara is the debut album by Mexican singer Ana Bárbara, released in 1994.  She was nominated for a Premio Lo Nuestro Award in two Regional Mexican categories, including Best New Artist.  She won her first Premio Furia Musical Award for Best New Artist.

Joss Stone: Joscelyn Eve Stoker (born 11 April 1987), better known by her stage name Joss Stone, is an English singer, songwriter and actress.  She rose to fame in late 2003 with her multi-platinum debut album, "The Soul Sessions", which made the 2004 Mercury Prize shortlist.  Her second album, the similarly multi-platinum "Mind Body & Soul" (2004), topped the UK Albums Chart for one week and spawned the top ten hit "You Had Me", Stone's most successful single on the UK Singles Chart to date.  Both the album and single received one nomination at the 2005 Grammy Awards, while Stone herself was nominated for Best New Artist, and in an annual BBC poll of music critics, Sound of 2004, was ranked fifth as a predicted breakthrough act of 2004.  She became the youngest British female singer to top the UK Albums Chart.  Stone's third album, "Introducing Joss Stone", released in March 2007, achieved gold record status by the RIAA and yielded the second-ever highest debut for a British female solo artist on the "Billboard" 200, and became Stone's first top five album in the US.

List of awards and nominations received by Mýa: American R&B-pop singer and actress Mýa Harrison released her self-titled debut album in 1998 under Interscope Records.  It spawned the singles "It's All About Me", "Movin' On", and "My First Night with You".  The album and its success helped her score Soul Train Music Award nominations for Best R&B/Soul or Rap New Artist and Best R&B/Soul Album – Female, a NAACP Image Award nomination for Outstanding New Artist, and a Billboard Music Award nomination for New R&B/Hip-Hop Artist of the Year.  Her guest featured vocals on "Ghetto Supastar (That Is What You Are)" led to her first Grammy nomination for Best Rap Performance by a Duo or Group.

Rufus Wainwright (album): Rufus Wainwright is the eponymous debut studio album by Canadian-American singer-songwriter Rufus Wainwright, released in the United States on May 19, 1998 through DreamWorks Records.  The album was produced by Jon Brion, with the exception of "In My Arms", which was produced and mixed by Pierre Marchand, and "Millbrook" and "Baby", which were produced by Brion and Van Dyke Parks.  Lenny Waronker was the album's executive producer.

Japan Record Award for Best New Artist: The Japan Record Award for Best New Artist (最優秀新人賞 ) is awarded annually.  Until the 10th Japan Record Awards it was called New Artist Award, since 11th — Best New Artist Award.  At present all nominees for the Best New Artist Award are awarded the New Artist Award.

Supporting paragraphs: Rufus Wainwright discography Rufus Wainwright (album)
Answer: Rufus Wainwright