1997–2001: Career beginnings

In 1997, Gary joined X-Teen, a hip hop group, where he met Gil.^[1] They released two albums. Gary later said that he had neither the looks nor the talent so they left the group. Gary and Gil then joined Honey Family.^[2] They released two successful albums in 1999 and 2000. The other members were Digitty, Miryo, Park Myung Hou, Jura, Young Poon, and Su-Jung. To date, the group is still acknowledged as one of the best hip hop groups of all time because of their unique blend of rapping styles.^[3]

Gary, Gil, and Diggity collaborated to form a "Leessam Trio" (sam means three in Korean), and released a compilation album called 2000 Korea in the year 2000.^[4] Diggity eventually left the group. Gil and Gary changed the name to "Leessang". Diggity later stated in an interview that part of the reason he left is because when success went to his head he felt like a celebrity.^[2]

2002–04: Leessang of Honey Family and Jae,Gyebal

Gil managed to borrow 2 billion won to fund their first album.^[5] With no formal musical training, the duo learned as they were producing by spending 400 hours straight inside the studio. Through their efforts, they managed to produce 60 songs.^[6] On June 27, 2002, Leessang released their first album, Leessang of Honey Family. Their breakaway hit was the title track featuring Jung-in. The song, "Rush", which uses an identical baseline to "You Are Everything" by the Stylistics and was released one day after Nelly's Grammy winning song - "Dilemma", won the hip-hop music awards from the Mnet KM Music Video Festival. Many credited the perfect blend of Jung-in, Gil and Gary's voices as one of the reasons for the song's success. This was also the beginning of their long partnership with Jung-in. "Rush" remains in Leessang's repertoire to date.^[7]

They released their second album, Jae,Gyebal (재,계발) on May 22, 2003. Jung-in once again provided the female vocals for their second hit song "Leessang Blues", written and composed by Gary. When they made their "best of" album titled Leessang Special, a workflow was developed that has loosely remained the same. Gary writes most of the lyrics, Gil does the music, and they both produce.^[8] Despite their success, they were still largely underground. Gary said in episode 98 of Strong Heart that they were so "unknown" that they were blocked by security when they came to receive their first major award.^[9]

2005–10: Mainstream breakthrough

Their mainstream breakthrough happened when they released their third studio album Library of Soul on October 14, 2005. On May 17, 2007, their fourth album Black Sun was released. Leessang said that every song on the album tells a story of their life. They eventually won Cyworld Digital Music Awards: Song of the Month when the song stayed on the charts for 4 straight weeks.^[10]

It took them two years to release their fifth album, Baekajeolhyeon. The title track, "Champion", was dedicated to boxer Yo-Sam Choi, who was very close to Gary and Gil. Choi died on the ring in 2008. Gary decided to direct the music video, which was a move that set the precedent on all their succeeding music videos.^[11]

In 2009, Leessang signed with a new label Jungle Entertainment, founded by hip-hop legend Tiger J.K. (a.k.a. Drunken Tiger). It was later reported that Jungle is one of the few labels that give their artists more artistic control and gives probably the highest percentage in rights and royalties. Leessang and Ryoo Seung-Bum toured to Sydney, Australia for the first time in this year with show producer Leonard Dela Torre.

They released their sixth album, Hexagonal on October 6, 2009. The lead single, "Girl Who Can't Break-Up and Boy Who Can't Leave" featured Jung-in once more. The song went straight to No. 1 on KBS Music Bank where it stayed at No. 1 for three weeks straight. Another song in the album, "Let's Meet Now", was a collaboration with the band Jang Gi Hwa and Faces. It was used for Fish & Grill's TV Commercial.

2011–17: Asura Balbalta, Unplugged and disbandment

Leessang's seventh album, Asura Balbalta, was released August 25, 2011. The title song, "I Turned off the TV", occupied the top position on Billboard's K-Pop Hot 100, and every other song from the album charted.^[12] "I Turned off the TV" was banned by all TV networks and radio stations because of explicit sexual content.^[13] However, it was reported to earn US$500,000 within the first month of release.^[14] Gary later said that they were becoming more comfortable talking about different sensitive issues as they age.^[2]

In 2011, LeeSsang embarked on their first nationwide solo tour titled Leessang Theatre. Gary revealed on Strong Heart (TV series) that the inspiration to his songs "Leessang Blues", "I'm Not Laughing", "Ballerino", "Girl Who Can't Break up, Boy Who Can't Leave" and "You're the Answer to a Guy Like Me" was his ex-girlfriend of almost 7 years.^[9]

In May 2012, Leessang released their eighth album, Unplugged. It was a fulfillment of their long time dream to collaborate with different artists from different genres, using a full band via an analogue recording. That same month, the duo announced that they created Leessang Company. They intended to create live events that were geared towards putting up quality and innovative live shows. Jungle Entertainment remains their label but they will produce and direct all their live shows under the new company.^[15]

On July 15, 2012, Gary and Gil were both featured on Psy's "Seventy Seven 101." Psy, Kim Jin Pyo, and Leessang all worked together on the song.^[16] The song and the album were restricted because of explicit lyrics in "Seventy Seven 101".^[17]

In December 2012, they performed a one-night only show with the band YB with whom they collaborated for the song "Someday", "Run" and "Madman". After strong public demand, they decided to do a short nationwide tour with YB. They also went to their first U.S. Tour. They had a show in New York and Los Angeles, and both were sold out.^[18]

On July 14, 2015, Leessang reached the top of multiple charts with their single "Kaleidoscope" featuring Mi Woo.^[19]

On April 6, 2017, it was reported that they may have disbanded as they have parted their own ways and work solely, after establishing their own music labels.^[20]

Studio albums

Compilation albums

Singles

Soundtrack appearances