John Mayer

A soulful singer to the core, John Mayer had a gift of writing sharp lyrics and a deft command of the guitar that was reminiscent of renowned blues guitarists like Eric Clapton and Buddy Guy. The Grammy Award-winning singer burst onto the pop scene with the album Room for Squares (2001), and easily made his mark as a sensitive crooner having a "quarter-life crisis" with songs such as "No Such Thing" and "Your Body Is a Wonderland."

Mayer's follow-up albums, Heavier Things (2003) and Continuum (2006), featured ballads like "Daughters" that displayed the acoustic rocker's vulnerabilities, as well as his reflections on bigger political and social issues like "Waiting on the World to Change." Yet, just a few years after scoring his first hit, Mayer quickly became a tabloid fixture for his serial dating habits. His conquests reportedly included some of Hollywood's most coveted beauties, but none were more salacious than his on-again-off-again trysts with singer Jessica Simpson and actress Jennifer Aniston.

Mayer landed in hot water after his shocking kiss-and-tell-all in a Playboy magazine interview, where he compared having sex with Simpson to craving crack cocaine and detailed the reason behind his split with Aniston. After a public flap over his controversial interview, Mayer tried to redeem himself by bringing the focus back to music. In 2009, he released the commercially successful album pop-rock Battle Studies, featuring openhearted lyrics and brilliant guitar-shredding skills that reminded everyone that Mayer was still one of the most dynamic and exciting musicians of all time.

John Clayton Mayer was born on Oct. 16, 1977 in Bridgeport, CT and raised in nearby Fairfield. The middle son of two teachers, he played the flute and violin in elementary school, and started playing the guitar at age 13, performing in local blues clubs solo and with a band called Villanova Junction. When he was 17, Mayer suffered a cardiac arrhythmia that sent him to the hospital for a weekend. The incident sparked an interest in songwriting for Mayer, who wrote his earliest lyrics the night he went home from the hospital.

After graduating from high school, Mayer worked as a gas station attendant and saved up money to buy a guitar. After spending a year at Boston's Berklee College of Music, Mayer dropped out and moved to Atlanta, GA, where he frequently performed at local blues clubs. The aspiring singer released his first album Inside Wants Out (1999), which he distributed himself while playing gigs. In 2000, after performing at the prestigious South by Southwest Music Festival in Austin, TX, Mayer received the break he has been waiting for and landed a contract with Aware Records, a subsidiary of Columbia Records.

Mayer immediately went to work on his first major label debut. In 2001, he released the album Room for Squares, where his breathy vocals and emotional vulnerability shone in pop ballads such as "Your Body is a Wonderland" and "No Such Thing." A sort of travelogue about his search for love and identity, the album reached No. 8 on the Billboard 200 and sold more than four million copies. In 2003, it earned the sensitive heartthrob a Grammy award for Best Male Pop Vocal Performance for "Your Body is a Wonderland" - a song that was rumored to have been written about Mayer ex, actress Jennifer Love Hewitt.

That same year, Mayer released his sophomore album, Heavier Things. Fueled by the upbeat single "Bigger Than My Body" and the sentimental ballad "Daughters," the album debuted at No. 1 on the Billboard 200 chart, and rewarded Mayer with two more Grammy awards for Best Male Pop Vocal Performance and Song of the Year. Yet, as successful as the pro-woman single "Daughter" was, Mayer told Rolling Stone magazine that it was too sappy and that he thought of it as "career death." The first of many such comments gave his fans and critics alike a sneak peek of Mayer's not-yet-seen other persona - a snarky yet self-deprecating artist with the inability to filter what comes out of his mouth.

He even attempted a stand-up comedy career, hosting a VH1 documentary special titled "John Mayer Has a TV Show" (2004) where he displayed seemingly uncharacteristic antics like wearing a bear suit while teasing concertgoers in the parking lot during one of his shows. In 2005, Mayer broke away from his pop heartthrob image and formed a guitar-driven jam band, The John Mayer Trio, with veteran session musicians Steve Jordan on drums and Pino Palladino on bass. Many saw his unexpected move as a significant departure from his trademark sensitive balladeer image.

He collaborated with artists from different genres such as Alicia Keys, Kanye West and B.B. King, and showed off his musical range by performing with his idols Stevie Ray Vaughan and Buddy Guy. The following year, Mayer released the album, Continuum, featuring the protest anthem "Waiting on the World to Change," as well as songs that veered toward relationships-gone-sour narratives. The blues- and R&B-infused platinum-selling album did bring Mayer two Grammy awards - Best Male Pop Vocal Performance and Best Pop Vocal Album - in 2006.

Over the years, Mayer's personal life consistently made headlines. He was notorious for racking up a long list of beautiful actress conquests, including Jennifer Love Hewitt, Minka Kelly and Cameron Diaz. He was also linked to country music darling Taylor Swift, who habitually wrote about her exes on her albums, and was rumored to have penned one about the guitar-wielding lothario. But it was the rocker's tumultuous affairs with pop singer Jessica Simpson and actress Jennifer Aniston that earned Mayer status as a tabloid regular.

Apart from his womanizing ways, his unfiltered comments also made news. In early 2010, Mayer became the topic of national controversy for using "the N-word" and comparing his sexual organ to a white supremacist in a no-holds-barred Playboy magazine interview. In the article, he also recalled his steamy relationship with Simpson, which lasted for nearly two years beginning in 2006. He revealed that he was "addicted" to the singer, and went on to compare her to "sexual napalm."

Shortly after the issue went on sale, a visibly offended Simpson went on "The Oprah Winfrey Show" (syndicated, 1986-2011) to say that she did not accept Mayer's apology for comparing her to crack cocaine. In contrast, Mayer was more discreet with his on-again, off-again relationship with Aniston, whom he started dating in spring 2008. In the same controversial Playboy interview, Mayer admitted that he had a hard time moving on after his split with Aniston and he was quoted saying it was one of the worst times of his life. The couple never reconciled after their 2009 break-up, which was allegedly caused by Mayer's inability to connect with Aniston, who was reportedly upset over the singer's excessive use of the social networking site, Twitter.

In between romancing Hollywood's leading ladies, Mayer released several commercial successes, including the album, Where The Light Is: John Mayer Live in Los Angeles (2008), featuring some of his biggest hits and his interpretations of covers like Tom Petty's "Free Fallin'" (1989). Mayer also topped the charts with the album Battle Studies (2009) featuring the pop tracks "Who Says," "Heartbreak Warfare," and "Half of My Heart." While the album debuted at No. 1 on the Billboard 200 chart and received mostly positive reviews from music critics, Mayer reportedly told Rolling Stone magazine that he thought the album was "not his best."