[10] In his last year of high school, Henry was chosen at the 2006 SM Entertainment Global Audition in Toronto;[14][15] he was one of two out of three thousand applicants who were recruited.

[23] Henry appeared as a violinist in South Korean group Super Junior's music video for "Don't Don" in September 2007.

[32] He featured on the track "Love Me" (Chinese: 愛我; pinyin: Ài wǒ) from label-mate Zhang Liyin's first single album, Moving On, which was released on October 29, 2009.

[24][38] He was featured on Jonghyun and Jinho's duet titled "Don't Lie" from SM the Ballad's first album Miss You, released on November 29, 2010.

[40] Henry's solo song "Off My Mind" (Chinese: 表白; pinyin: biǎo bái) was included in Super Junior-M's second EP Perfection which was released on February 25, 2011.

[43] In March 2012, he featured on BoA's single "One Dream" alongside Key which served as the opening song for SBS's audition program K-pop Star.

[45][46] He became a member of the project group Younique Unit with Eunhyuk, Taemin, Kai, Luhan, and Hyoyeon, for a collaboration between SM Entertainment and Hyundai.

[47] The same year, Henry was cast as the lead in his film debut, Final Recipe, alongside Malaysian actress Michelle Yeoh.

[48] The film tells the story of young aspiring chef Mark, played by Henry, who participates in an international cooking contest to save his grandfather's restaurant from going out of business.

[49] In preparation for the role, Henry studied under chef Lee Yeon-bok [ko] and practised cooking 3–4 hours a day for several months.

[24] NoizeBank is a music production team comprising Henry and his Berklee classmates Gen Neo, Neil Nallas, and Isaac Han.

[57][58] In February 2014, Henry joined the cast of the Korean military-variety show Real Man with fellow celebrities Chun Jung-myung, Park Gun-hyung, K.Will.

[68] In January 2015, Henry made his Korean acting debut in Mnet's music drama Persevere, Goo Hae-Ra [ko].

Throughout 2016, Henry became more active in China appearing in a slew of reality shows including Sisters Over Flowers 2 and Are You Normal 3 [zh],[74] the latter of which he hosted with He Jiong.

[78]Henry appeared on the Chinese reality show Back to Field, which aired in January 2017, as one of the three fixed cast members alongside He Jiong and Huang Lei.

His appearance led to an increase in the show's ratings and he attracted attention for using live loops to reinterpret "Uptown Funk".

The lyrics expresses the heartfelt sadness and longing for a past lover, which correlates with the Korean title of the song "그리워요" (lit.

On April 29, 2017, he released the single "Real Love" (Korean: 사랑 좀 하고 싶어; Revised Romanization: Sarang jom hago sipeo) and its acoustic version on May 10.

He also rearranged Yoon Jong Shin's 1996 song, "Rebirth", for Red Velvet and released the collaboration single "U&I" with Sunny on the show.

[89] In January 2018, it was announced that Henry will arrange and perform a new version of the 1986 song "Daughter's Love" (Chinese: 女兒情; pinyin: nǚ ér qíng) for the soundtrack of the film The Monkey King 3.

[100] In November 2018, Henry announced that he had joined Monster Entertainment Group, an agency based in South Korea that he founded with his brother, Clinton, to help build his brand globally.

[103] On December 26, 2018, South-Korean band g.o.d announced they would be releasing a special 20th anniversary album titled Then & Now, which will feature a remake of the group's 2001 song "Road," rearranged by MeloMance's Jung Dong-hwan and sung by Henry, IU, Urban Zakapa's Jo Hyun Ah, and Yang Da-il.

[107] He released the single "Don't Forget" (Korean: 한강의 밤; Revised Romanization: Hangangui bam) in October which was co-written by and features indie duo Rocoberry.

[109] He also appeared as a judge on the Chinese reality shows Dance Smash [zh] and Miss Voice in the last quarter of the year.

[115] On September 17, 2020, Henry featured in "Take Over", the official song of the 2020 League of Legends World Championship, alongside Jeremy McKinnon and MAX.

[119] SeoulBeats described the album as "captivating" in their review and noted that it "[gives] nods to his complicated musical past", being a multi-instrumentalist and idol turned singer-songwriter.

[120] The writer notes Henry's "penchant for interesting instrument choices, loop peddles [sic], and electronic mixing" that makes Journey "[stand] out from most other solo releases as of late".

[121] In August 2021, he joined the fourth season of Street Dance of China as one of the four team captains alongside Wang Yibo, Lay Zhang, and Han Geng.

In October 2021, Henry's artwork was featured at the START Art Fair held at London's Saatchi Gallery as part of a special exhibit recognising K-pop's global influence.

[130][131] In May 2020, the Ministry of Culture, Sports and Tourism named Henry as the promotional ambassador for El Sistema Korea, also known as Orchestra of Dream, which supports the musical education of children and young people including those who are underprivileged.