In 1989 Red Flag released "Naive Art". Several singles from the album charted highly on the US Billboard "Hot Dance Music/Club Play" charts, such as "Russian Radio" (11) and "If I Ever" (12). Red Flag went on to appear on American Bandstand, and the video for "Russian Radio" was played by MTV's 120 Minutes. Notable producers who worked on Naive Art include Paul Robb of synthpop band Information Society and Joseph Watt of remix service Razormaid. Naive Art remains the only full album Razormaid ever produced.

Red Flag toured frequently, playing at first as opening act to New Wave and synth-pop artists such as Devo, Thomas Dolby, Book of Love and Real Life.

Since then, Red Flag released 11 albums, 14 CD singles, two box sets and appeared on numerous compilations. Their music has been featured on MTV reality shows. The band has played concerts around the world in the U.S., Europe, Canada, Mexico, and South America. Their work has inspired countless bands and garnered fans around the globe
After the death of Mark Reynolds in 2003 Red Flag was in a brief limbo, until Chris Reynolds re-launched Red Flag in 2007 with a darker, harder and more edgy sound than ever before but still retains the bands heritage in sound.

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