Taylor's life took an unusual turn in 1979 when he was first of the 100 chosen, from 20,000 applicants, to spend the summer at John Davidson's summer camp. At the camp, Taylor spent time learning from singers like Tony Orlando, Florence Henderson, and John Davidson. Also that year, Taylor heard one of his biggest influences, The Clash's London Calling. "It saved my life, musically," said Taylor.

After recording a demo of original songs, Taylor began to write for the musical group The Continentals. He recorded his debut solo project I Want To Be A Clone in 1982 and released it in January, 1983. He quickly gained a reputation for writing songs that attacked beliefs, practices, or people that he disagreed with. In 1984, Taylor recorded his first full length album, Meltdown with some of the demo material that was not included on Clone plus some new material. His video single of the title track, "Meltdown (at Madame Tussaud's)" was played on MTV, which was unusual for a Christian artist at the time. The video featured an appearance by actress Lisa Whelchel. The album also included "We Don't Need No Colour Code", which attacked Bob Jones University and its anti-interracial dating policy (Bob Jones University abandoned this rule in 2000). ("Guilty By Association", one of the recycled demo songs, includes a jab, with an impression in the middle eight, at televangelist Jimmy Swaggart. Swaggart struck back later by devoting part of a chapter of Religious Rock 'N' Roll, a Wolf in Sheep's Clothing (ISBN 0-935113-05-3) to Taylor, whom he saw as playing evil rock music.)

Taylor followed that release with On The Fritz, produced by Foreigner's Ian McDonald. Fritz, keeping with Taylor tradition, took aim once again at religious leaders. This time, his targets included Bill Gothard ("I Manipulate"), greedy TV evangelists (again) ("You Don't Owe/a/ Me Nothing"), politicians using religion or avoiding questions of morality in order to get votes ("It's A Personal Thing"), and public schools teaching "values clarification" to children, asking them to determine who should be thrown overboard in an overcrowded lifeboat ("Lifeboat").

In 1987, Taylor once again lived up to his controversial reputation with a song called "I Blew Up The Clinic Real Good". The song criticizes anyone who claims to be a pro-life activist who would blow up abortion clinics or kill doctors. Unfortunately, the point of the song was lost on many and resulted in Taylor's album, I Predict 1990, being pulled from the shelves at some Christian record stores. Taylor himself would occasionally call those stores to explain the song to them.

With 1990, Taylor's targets included mainstream universities ("Since I Gave Up Hope I Feel A Lot Better", featuring fiddle work from Papa John Creech of Jefferson Airplane and Hot Tuna). Other tracks included "Jim Morrison's Grave", which once again brought Taylor some MTV exposure, and the Flannery O'Connor inspired "Harder to Believe Than Not To". Some stores also pulled the album as they thought the cover looked like a Tarot Card. Taylor then took a break from music, until 1990 when he returned as the lead singer of Chagall Guevara. Their first recording was "Tale o'the Twister," which appeared on the soundtrack to the 1990 film Pump Up the Volume. The band released their only album, the self titled Chagall Guevara, in 1991 on MCA records that year. A follow up album was begun, but not finished before the band was released from its contract, following slow sales for their debut.

Taylor returned with another solo album, Squint, and a live CD, Liver, in the mid 1990's. Squint included the track "Smug", which mocks Rush Limbaugh and Barbra Streisand, as ironic masters of smugness. The album also included the song "Cash Cow", which takes a jab at yet another televangelist, Robert Tilton. A tribute to Taylor entitled I Predict A Clone was released in 1994, which features performances by Sixpence None the Richer, Fleming and John, Starflyer 59, and others. In the years following those releases, Taylor focused his efforts on running a record label, Squint Entertainment, and producing projects for other artists, including Sixpence None the Richer's self titled 1997 release that featured the hit singles "Kiss Me" and a cover of The La's "There She Goes".

He would be most noted for his work with Newsboys.

Squint Entertainment lost its financial backing in 2001 and Taylor was forced out of the company. Taylor is currently working full time as a film maker and has directed music videos for Fleming and John, Rich Mullins, Sixpence None the Richer, Newsboys, Guardian, and two video albums for himself. While still running Squint, Taylor had begun work on a film project called St. Gimp, co-written with Ben Pearson and Willie Williams. That film was abandoned with the company. He co-wrote and directed the feature film The Second Chance starring Michael W. Smith, released February 17, 2006. He also directed the relatively little known Newsboys movie "Down Under The Big Top" in which the band stars.

Taylor appears in the documentary film Why Should the Devil Have All the Good Music? (released on DVD in 2006), in interview segments and performing part of "We Don't Need No Colour Code."