Having started in the left of center before moving to the right, by the mid-2000s he had moved back to the political left, on WEVD, and finally on WOR.
His last scheduled broadcast was in Boston, Massachusetts, his Jay Diamond Show appearing on WRKO until 2005.He is a voice impressionist and has given short radio plays performed by "The Mighty Diamond Art Players," all of whom are himself.
One of his famous impersonations was of Al Sharpton.
Diamond also parodied the speaking style of other New York City politicians, such as then-Governor Mario Cuomo and former Mayor Ed Koch.
In 2009 he wrote an opinion essay for the Buzzflash site, "Talk Radio is a Cancerous Blight on the Nation, Not 'Entertainment.'"