Born to a Jewish family in Brooklyn, and raised in Freeport, New York, on Long Island, Schaap began writing a sports column aged 14 for the weekly newspaper Freeport Leader, but the next year he obtained a job with the daily newspaper The Nassau Daily Review-Star working for Jimmy Breslin.

Opposing the grandiose and self-important nature of the National Football League's championship match, he hired two Los Angeles Rams players, Fred Dryer and Lance Rentzel, to cover Super Bowl IX.

Donning costumes inspired by The Front Page, "Scoops Brannigan" (Dryer) and "Cubby O'Switzer" (Rentzel) peppered players and coaches from both the Minnesota Vikings and Pittsburgh Steelers with questions that ranged from the clichéd to the downright absurd.

In 1988 he began hosting The Sports Reporters on ESPN cable television, which in later years often featured his son Jeremy as a correspondent.

He wrote the 1968 best-seller Instant Replay, co-authored with Jerry Kramer of the Green Bay Packers, and I Can't Wait Until Tomorrow... 'Cause I Get Better-Looking Every Day, the 1969 autobiography of New York Jet Joe Namath.

Other books included a biography of Robert F. Kennedy; .44 (with Jimmy Breslin), a fictionalized account of the hunt for Son of Sam killer David Berkowitz; Turned On, about upper middle-class drug abuse; An Illustrated History of the Olympics, a coffee-table book on the history of the modern Olympic Games; The Perfect Jump, on the world record-breaking long jump by Bob Beamon in the 1968 Summer Olympics; My Aces, My Faults with Nick Bollettieri; Steinbrenner!, a biography of mercurial New York Yankees owner George Steinbrenner; and Bo Knows Bo with Bo Jackson.

Schaap died on December 21, 2001, at Lenox Hill Hospital in New York City of complications from hip replacement surgery that September.

Specifically, they alleged that, for two years before his surgery, Schaap had been given a powerful medication called amiodarone to treat an irregular heartbeat.

Three days after the surgery, Schaap began having difficulty breathing, and he was subsequently diagnosed with acute respiratory distress syndrome.

In the same year, he was also inducted into the Nassau County Sports Hall of Fame, which created a Dick Schaap Award for Outstanding Journalism.