performers to set up more writing appointments. Anderson, who was not used to writing with others, decided to make adaptations to his own songwriting style in order to collaborate. "I let a lot of young kids tell me a lot of things, and I benefited from that, greatly", he recounted. Anderson began co-writing more frequently during the 1990s. Wariner had another hit in 1999 with another Anderson composition titled "Two Teardrops". The song became a major hit when it reached number two on the country songs chart in June 1999. The song was also nominated for a Grammy award. During the same period, he collaborated with Skip Ewing and Debbie Moore on the song "Wish You Were Here". The song was released as a single by Mark Wills and became a number one hit on the Billboard country chart in 1999. Anderson later commented that the song's success helped him resolve financial struggles he had battled during the decade. He followed "Wish You Were Here" with the song "A Lot of Things Different", which was co-written with Dean Dillon. The song was written during an exchange the pair had while out to breakfast. The song was later recorded by Kenny Chesney, whose version reached number six on the country singles chart in 2003. Chesney's song was followed by a track later recorded by Brad Paisley and Alison Krauss called "Whiskey Lullaby". The tune was composed with singer-songwriter Jon Randall. After writing the song, Randall was reluctant to record a demo of the record to pitch to other artists. However, Anderson believed the song could be a success and its demo was then recorded at ten o'clock on a weeknight. Paisley's version was released as a single in 2004 and peaked at number three on the Billboard country chart that year. In 2005, "Whiskey Lullaby" won "Song of the Year" at the Country Music Association Awards. Anderson recalled the excitement of winning the accolade in his autobiography: "I jumped up and hugged Brad and knocked his white western hat from his head." In 2006, Anderson co-wrote a song with Jamey Johnson and Buddy Cannon called "Give It Away". The song would later be cut by George Strait. The song's concept was inspired by Johnson's divorce at the time and included a spoken narration, a device that was not popular in the country genre during the mid-2000s. Strait's version was released as