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.

[4] The song's musical structure features an introductory guitar sound, followed by a soaring chorus, and heavy beating drums.

[7] 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".

Jenny Eliscu of Rolling Stone wrote that "Rough Landing, Holly" and "Lights and Sounds", the latter being the title track, "boast seismic alt-rock riffs and mosh-worthy refrains.

"[15] Tom Beaujor of Entertainment Weekly reported that the song was a "blustery tale of puppy love gone to the dogs that will surely make for a great ringtone.

"[16] Sputnikmusic wrote: "So how typical to have the next song, 'Rough Landing, Holly', slap you right on the mouth with a face-melting violin solo.

Songs like the title track, 'Rough Landing, Holly,' and 'Down on My Head' are tightly crafted, state-of-the-art examples of shiny, earnest punk-pop that sounds sunny even when it's sad".

[18] Tony Pascarella of AbsolutePunk.net noted that "we see flashes of the 'old' band on 'Rough Landing, Holly', but it’s not nearly widespread enough for my liking (although the song is possibly the best one on the new album).

It refers to that world, and I liked the idea of paralleling the band's experiences over the past two years with some of the things [frontman] Ryan [Key] is going through in this video.

"[1] Webb went on to add that the reason Key is sprinting through Los Angeles, once again, is not bad guys that are after him, it is his "own personal demons".

[1] Webb concluded that before filming began for the video, he had wanted to learn the experience that Key and bassist Peter Mosely were going through in New York, as they moved there to begin working on Lights and Sounds, and about the things they saw while they were there.

Someone dressed in dark clothing gestures to offer him a drink, when Key notices he is in a bar filled with Asian people.