Medeiros began his musical career at the age of 10 when he helped his father entertain guests on his tour bus on the island of Kauai. In 1986, at the age of 16, Medeiros won a local radio talent contest in Hawaii when he performed a cover version of George Benson's "Nothing's Gonna Change My Love for You" which was subsequently produced into an album by a small local independent label. A visiting radio executive, Guy Zapoleon, from KZZP in Phoenix, Arizona heard the song and took the record back to Phoenix, where, through word of mouth, it became a national hit. Later, a worldwide hit, it reached #12 on the Billboard Hot 100 and spent four weeks at number one on the UK Singles Chart in July 1988. It reached #3 on Billboard's Adult Contemporary chart.
In 1988, he recorded the single "Un Roman d'amitié" (Friend You Give Me a Reason), a duet in French with Elsa Lunghini. He also achieved a 1990 United States #1 hit duet with Bobby Brown titled "She Ain't Worth It". The same track peaked at #12 in the UK Singles Chart. He had another hit duet with Ray Parker, Jr. titled "All I'm Missing Is You" which peaked at #32 in the US. In 1989, Medeiros recorded "Under Any Moon" with The Jets, which was included on the soundtrack of The Karate Kid Part III.
Medeiros' relationship with the British media somewhat soured in 1990 when he was seemingly ridiculed on the music review program Juke Box Jury. A panel consisting of footballer John Fashanu, singer Neneh Cherry and comedians Vic Reeves and Bob Mortimer, overseen by Jools Holland, slated the video of "All I'm Missing Is You". Unbeknownst to the guest reviewers at the time, Medeiros was present and live in the studio, watching their commentary. Emerging afterwards as that week's "special guest", all parties were visibly embarrassed, with Medeiros exiting the set swiftly. This moment was later included in both Channel 4's TV Hell program.
In 1992 Medeiros recorded a duet with Thomas Anders (of Modern Talking fame) titled "Standing Alone" and shot a video.
Medeiros wrote "Break These Walls" for the New Zealand singer, Sam Verlinden. He also wrote the song "Follow the Sun" for Regine Velasquez which was later recorded by the group Forte. In addition, Medeiros wrote the song entitled "These Tears I Cry" for Martin Nievera. Medeiros has written nearly two hundred songs, many of which have been recorded by various artists throughout the world.
Dr. Medeiros is the host and performer at the Hale Koa Hotel's luau in Waikiki, and was the Vice Principal of Maryknoll Grade School. He has taught grades K, 2, 3, 4, 5, 8, and high school at various schools throughout Oahu starting in both public and private schools including Mililani Middle School, St. Joseph School in Waipahu, Island Pacific Academy in Kapolei, and Maryknoll High School. Medeiros also headlined in Waikiki for many years with Frank Delima, one of Hawaii's most famous and seasoned comedians.
On July 1, 2015, Medeiros was appointed President of St. Louis School, an all boys Catholic (Marianist Order) school (K-12) in Honolulu Oahu.
Medeiros is of Portuguese ancestry. When finished touring, he was an excellent student in the Humanities, Literature, and History and graduated from The University of Hawaii-West Oahu with a BA in History and The University of Phoenix-Hawaii with an MA in Elementary Education. In May 2014, Medeiros received his doctorate degree in Education from the University of Southern California.
Medeiros and his wife, Tammy, have been married since 1996. They have a son, Chord, and a daughter, Lyric.Glenn Medeiros (1987) US #83Not Me (1988) UK #63Glenn Medeiros (1990) (1990) US #82It's Alright to Love (1993; Europe and Asia only)The Glenn Medeiros Christmas Album (1993)Sweet Island Music (1995)Captured (1999)ME (2003)With Aloha (2005)Aloha from Paradise (2007) (various artists)It´s Alright to Love (2016)