The song was released on May 6, 2006, as the second single from Lights and Sounds and reached number 27 on Billboard's Hot Modern Rock Tracks chart. Internationally, the track appeared for one week in the Australian and New Zealand charts at number 49. "Rough Landing, Holly" was well received by music critics, who noted the track's general sound. After its release, it was featured in the soundtrack of the 2006 video game, FlatOut 2.
The music video was directed by Marc Webb, who had previously collaborated with the band on their previous music videos. In an interview, Webb revealed the video was the sequel to the band's 2004 video "Ocean Avenue". Webb also revealed that unlike "Ocean Avenue", in which Key is running away from bad guys, this video shows Key running away from his "own personal demons".
While Yellowcard was working on their upcoming album, Lights and Sounds, they developed a character, Holly Wood, who served as a narrator and protagonist for the album's storyline. The character also came about when the band began writing about their hatred for life in Los Angeles. Vocalist Ryan Key, in discussion of the character, said, "Holly became this person on the record who appears in a lot of the songs, and at times you love her and at times you hate her. At times she's good to you and sometimes she's bad." Violinist Sean Mackin, also in discussion of the character, said: "...Ryan didn’t have a romantic interest in his life and he didn’t want to write 'Only One' again, and he wanted to create something new. A lot of songwriters narrate and create fictional characters ... and Holly was a character where sometimes you love her and sometimes you hate her, and she was someone he could get all his emotions out through." Key revealed that the song "Rough Landing, Holly", which features the Holly character, was his "favorite song" from Lights and Sounds.
Written in the key of E major, the beat is set in common time and moves at a moderate 175 beats per minute. The song's musical structure features an introductory guitar sound, followed by a soaring chorus, and heavy beating drums. Sean Mackin plays the violin in "Rough Landing, Holly". During discussion of the track listing in Lights and Sounds, Yellowcard revealed that "Rough Landing, Holly" spoke about the "difficulty of giving up its allure". The band explained the lyrics, "And I still can't get out / She's all I think about / Can't let her go/ ...She moves fast, takes control / And like a heart attack I know I can't turn back", were written because of that particular reason.
"Rough Landing, Holly" was released to radio on April 11, 2006. "Rough Landing, Holly" was released in the United States on May 6, as the second single from Lights and Sounds. The song peaked at number 27 on Billboard's Hot Modern Rock Tracks chart. Internationally, the track appeared on both the Australian Recording Industry Association (ARIA) and New Zealand charts at the number 49 position, and individually spent one week on the charts. "Rough Landing, Holly" was featured in the soundtrack of the 2006 video game, FlatOut 2.