Born Michael Anthony Orlando Cassavitis, he was raised in New York's notorious "Hell's Kitchen" in Manhattan. His best friend was fellow Puerto Rican Freddie Prinze. One of their bonding factors was their common Puerto Rican ancestry.

His musical career started with The Five Gents, a doo-wop group he formed. His first success came when he recorded the hit"Halfway To Paradise" After becoming general manager at Columbia Records, he was tempted back to a recording career when he was asked to record a demo record of "Candida." The label liked the demo so much that Tony's performance was released, under the band name "Dawn" (the name of a record executive's daughter). Joining Tony were Telma Hopkins and Joyce Vincent Wilson, and the trio scored a string of number ones with "Tie A Yellow Ribbon 'Round The Old Oak Tree", "Knock Three Times" and "Candida".

"Tie A Yellow Ribbon..." was a huge hit in 1973. Its story concerned a man just out of prison riding home on a bus. If his wife tied a yellow ribbon around a certain oak tree, it would signal she had forgiven him, and he could return home. Eight years later the symbol of a yellow ribbon tied around a tree (or anything else) was popular as a sign of solidarity with the American hostages in Iran. The symbol of a yellow ribbon continues to indicate support for troops overseas.