"Stupid Boy" written by Dave Berg, Deanna Bryant and Sarah Buxton. First recorded by Sarah Buxton, it was later recorded by Australian country music singer Keith Urban on his 2006 album Love, Pain & the Whole Crazy Thing, from which it was released as that album's second single in December 2006. A year after its release, the song won Urban a Grammy Award for Best Male Country Vocal Performance.

Urban told Billboard that he recorded "Stupid Boy" at the suggestion of his wife, actress Nicole Kidman. He also noted how the song's subject matter contrasted with the more up-tempo love song "Once in a Lifetime," the album's first single, saying that the two songs were "yin and yang."Sarah Buxton, who co-wrote the song, recorded a version before Urban did. This version was included on a 2007 extended play entitled Almost My Record as well as Buxton's 2010 self-titled album.

Tamara Conniff and Ray Waddell of Billboard described the song as "a ballad on how men foolishly break the hearts of the women they love."Associated Press reviewer Michael McCall called it "a funky, witty take on a guy who can't appreciate how good he has it."

Keith Lionel Urban (born 26 October 1967) is a Australian country music singer, songwriter and guitarist whose commercial success has been mainly in the United States and Australia. Urban was born in New Zealand and began his career in Australia at an early age. In 1991, he released a self-titled debut album, and charted four singles in Australia before moving to the United States in 1992. Eventually, Urban found work as a session guitarist before starting a band known as The Ranch, which recorded one studio album on Capitol Records and charted two singles on the Billboard country charts.

Still signed to Capitol, he made his solo American debut in 1999 with the album Keith Urban. Certified platinum in the U.S., it also produced his first American Number One in "But for the Grace of God". His breakthrough hit was the Number One "Somebody Like You", from his second Capitol album Golden Road (2002). This album also earned Urban his first Grammy Award win for "You'll Think of Me", its fourth single and the fourth Billboard Number One of his career. 2004's Be Here, his third American album, produced three more Number Ones, and became his highest-selling album, earning 4× Multi-Platinum certification. Love, Pain & the Whole Crazy Thing was released in 2006, producing the record-setting No.17 country chart debut of "Once in a Lifetime", as well as Urban's second Grammy for the song "Stupid Boy", while a Greatest Hits package entitled Greatest Hits: 18 Kids followed in late 2007. This album was re-released a year later as Greatest Hits: 19 Kids with one track added: the number one "You Look Good in My Shirt", which he had previously recorded on Golden Road. Additional albums Defying Gravity and Get Closer were released on 31 March 2009 and 16 November 2010, respectively.

Taylor Alison Swift (born December 13, 1989) is an American singer-songwriter and occasional actress. Raised in Wyomissing, Pennsylvania, Swift moved to Nashville, Tennessee at the age of fourteen to pursue a career in country music. She signed to the independent label Big Machine Records and became the youngest songwriter ever hired by the Sony/ATV Music publishing house. The release of Swift's self-titled debut album in 2006 established her as a country music star. "Our Song", her third single, made her the youngest sole writer and singer of a number one song on the country chart. She received a Best New Artist nomination at the 50th Grammy Awards.

Swift's second album, Fearless, was released in late 2008. Buoyed by the chart success of the singles "Love Story" and "You Belong with Me", Fearless attracted a crossover audience and became the top-selling album of 2009. The record won four Grammy Awards, with Swift becoming the youngest ever Album of the Year winner. Fearless also received Album of the Year plaudits at the American Music Awards, Academy of Country Music Awards and Country Music Association Awards, making it the most awarded album in country music history. In 2010, Swift released her third album, Speak Now, which sold over one million copies in its first week. She then embarked on the 111-date Speak Now World Tour, which was attended by over 1.6 million fans and has become one of the highest-grossing concert tours of all time. The album's third single, "Mean", won two Grammy Awards for Best Country Song and Best Country Solo Performance. Swift is currently recording her fourth studio album, due for release in the fall of 2012.

Cassadee Blake Pope (born August 28, 1989) is an American singer-songwriter and musician and the lead vocalist of the pop punk band Hey Monday. With the band she has released a studio album, Hold on Tight and three extended plays. She went solo after Hey Monday's hiatus which was announced in December 2011, but reassured fans that the band was not "broken up." In early 2012 she played her first acoustic solo tour.

Escape the Fate is an American post-hardcore band from Las Vegas, Nevada formed in 2005 and originally from Pahrump, Nevada. They have released three EPs and three full-length studio albums. Dying Is Your Latest Fashion was the band's debut album and only album to feature vocalist Ronnie Radke. This War Is Ours, released on October 21, 2008, was the band's first album with Craig Mabbitt as the new lead vocalist. Their self-titled third studio album was released on November 2, 2010, first on the major label, DGC/Interscope, and their most successful album to date.

Before forming Escape the Fate, vocalist Ronnie Radke, bassist Max Green, drummer Robert Ortiz, lead guitarist Bryan Monte Money, and rhythm guitarist Omar Espinosa were in multiple bands all together. Monte Money later created Escape the Fate, and invited Omar Espinosa, who then invited Max Green into the band. Max Green later invited Ronnie Radke and Robert Ortiz, and later recruited Carson Allen.

In September 2005, Escape the Fate had won a local radio contest judged by My Chemical Romance. The gig awarded them the opportunity to open a show on the band's headlining tour with Alkaline Trio and Reggie and the Full Effect, which subsequently led to Escape the Fate's record deal with Epitaph. Following their record deal, the band released their debut EP titled There's No Sympathy for the Dead. in May 2006 which included two songs that were later on their full length album, Dying Is Your Latest Fashion. The EP was produced by Michael Baskette and helped earn the band attention from record labels and fans alike. After the EP's release, keyboardist Carson Allen left the band to join On the Last Day (Which he had also left to start another band called Me vs. Myself).