[2][3] For 30 years, he constructed a puzzle every Sunday for the San Francisco Chronicle (originally the San Francisco Examiner), which he syndicated to more than 50 Sunday newspapers,[4] including the Washington Post, the Los Angeles Times, the Philadelphia Inquirer, the Seattle Times, The Plain Dealer (Cleveland, Ohio), the Hartford Courant, the New York Observer, and the Arizona Daily Star.

This trend was encouraged by The New York Times crossword puzzle editor Will Shortz, who sought to appeal to a wider and younger readership with "pop culture references ... humorous word play, and ... unique and clever themes".

Reagle created the National Brain Game Challenge, an online contest featuring a Sunday crossword that contains a clued secret message.

[13] The New York Times crossword puzzle editor Will Shortz has said that "his [Reagle's] themes are consistently fresher and funnier than anyone else's.

It included the theme entries I'M IN A / RUSH, NO PICTURES, PLEASE, OR / ELSE YOU'LL LEARN THE / BLACKENED EYE WAY / THE RECORD SHOWS / I'LL BUST YOUR / NOSE IF YOU GET IN... / MY WAY.

[5] Other much-discussed puzzles carried titles like "Inappropriate Muzak for a Doctor's Office" and "Least Popular Beanie Babies".

[6] The 2006 documentary Wordplay depicted Reagle's on-camera construction of a crossword that subsequently was published in The New York Times.

The film then showed various famous crossword enthusiasts, including Bill Clinton, Jon Stewart, the Indigo Girls, and Mike Mussina, attempting to solve the puzzle.

[19] On November 16, 2008, Reagle was a "special guest voice" on an episode of The Simpsons called "Homer and Lisa Exchange Cross Words."