[1] Initially marketed as K-pop idols, the duo later developed a more mature image and became one of the most popular R&B groups in South Korea.

Hwang Yoon-Suk, later to be known as Hwanhee, was encouraged to audition by a staff member working for the label at his high school festival.

Unlike their predecessors on their label, popular teen idols at that time, they shied away from upbeat techno and dance music, opting for mid-tempo ballads.

[5] At the same time, the duo failed to rise to instant stardom unlike their predecessors such as H.O.T., whose album sales have passed the one million mark.

In the same year, the label released a female duo that was said by fans to complement Fly to the Sky known as Isak N Jiyeon, however the two groups never worked independently with each other.

Their 2003 studio album Missing You featured more tracks that departed from bubblegum music and emphasized their vocal skills for an image as serious artists.

[9][10] Nevertheless, they held their first official concert successfully in Jamsil Arena on December 21, 2004, and received "Best R&B Artist" award from SBS Gayo Daejun.

[14] Under this label, Fly to the Sky released their sixth studio album Transition after a year-long hiatus in January 2006.

[15] To commemorate the success of Transition, Fly To The Sky released a special new edition, which included music videos, deleted scenes and the additional tracks "Hwan Sang (Illusion)," "Hot and Cold," and "When I Say."

He admitted that the two had difficulties in the early days of their career and said that he had been troubled by feelings of inferiority to Hwanhee, because he received more attention and praise than him.

Hwanhee appeared on Korean television drama "Over the Rainbow" during summer of 2006, and Joo released his solo album The Brian in December 2006.

[21] Popular tracks that are included in the album are "Oneuldo Eebbeungul," ("오늘도 이쁜걸" Pretty Today Too) "Geuraedo Sarangipnida," ("그래도 사랑입니다" It's still love) and "Gee-uk Han Joom" ("기억 한 줌" Grain of Memory),[22] as well as "My Angel", which peaked at #1 on many on- and offline charts.

Decennium (2009) became the group's final album, with the duo stating that they will not renew their contract and will go their separate ways professionally.

Hwanhee has also participated in the production of Song Ji Eun's solo single "Yesterday" and also features in the title track.

[25] In June, the duo releases a music video titled "Years Apart" as a theme song for the movie No Tears for the Dead.

Brian predicts that there will no longer be any opportunity to include his rap in their album, and dislikes "being generalized as a duo comprised of one rapper and one vocalist."

The duo has been criticized for lack of creative control over their works and relying heavily on composers whose distinct styles overpower their vocals.

[29][30] Music critic Shin Hye Rim says,[29] Ironically, Fly to the Sky's sixth album Transition, which means change or transformation, shows no significant improvement.

Fany's thick tone color and Brian's clean-cut voice fuse to make music that spits out sorrow.