Barry began his journalism career in 1971, working as a general-assignment reporter for the Daily Local News in West Chester, Pennsylvania, near his alma mater, Haverford College.
He covered local government and civic events and was promoted to City Editor after about two years.
He also started writing a weekly humor column for the paper and began to develop his unique style.
He remained at the newspaper through 1974.
He then worked briefly as a copy editor at the Associated Press's Philadelphia bureau before joining Burger Associates, a consulting firm.

At Burger, he taught effective writing to business people.
In his own words, he "spent nearly eight years trying to get various businesspersons to...stop writing things like 'Enclosed please find the enclosed enclosures,' but...eventually realized that it was hopeless."

In 1981 he wrote a humorous guest column in the Philadelphia Inquirer about watching the birth of his son, which attracted the attention of Gene Weingarten, then an editor of the Miami Herald's Sunday magazine Tropic.
Weingarten hired Barry as a humor columnist in 1983.
Barry's column was syndicated nationally.
Barry won a Pulitzer Prize for Commentary in 1988 for "his consistently effective use of humor as a device for presenting fresh insights into serious concerns."

Barry's first novel, Big Trouble, was published in 1999.
The book was adapted into a motion picture directed by Barry Sonnenfeld and starring Tim Allen, Rene Russo, and Patrick Warburton, with a cameo by Barry (deleted in post-production).
The movie was originally due for release in September 2001 but was postponed following the September 11, 2001, attacks because the story involved smuggling a nuclear weapon onto an airplane.
The film was released in April 2002.

In response to a column in which Barry mocked the cities of Grand Forks, North Dakota, and East Grand Forks, Minnesota, for calling themselves the "Grand Cities", Grand Forks named a sewage pumping station after Barry in January 2002.
Barry traveled to Grand Forks for the dedication ceremony.

Articles written by Barry have appeared in publications such as Boating, Home Office Computing, and Reader's Digest, in addition to the Chicken Soup for the Soul inspirational book series.
Two of his articles have been included in the Best American Sportswriting series.
One of his columns was used as the introduction to the book Pirattitude!:
So You Wanna Be a Pirate?
Here's How! (
ISBN 0-451-21649-0), a follow-up to Barry's role in publicizing International Talk Like a Pirate Day.
His books have frequently appeared on the New York Times Best Seller List.

On October 31, 2004, Barry announced that he would be taking an indefinite leave of absence of at least a year from his weekly column to spend more time with his family.
In December 2005, Barry said in an interview with Editor and Publisher that he would not resume his weekly column, although he would continue such features as his yearly gift guide, his year-in-review feature, and his blog, as well as an occasional article or column.

In 2005, Barry won the Walter Cronkite Award for Excellence in Journalism.

On Sunday, September 22, 2013, the opening night of the 15th annual Fall for the Book festival in Fairfax, Virginia, Barry was awarded the event's highest honor, the Fairfax Prize, honoring outstanding literary achievement, presented by the Fairfax Library Foundation.
Barry began his journalism career in 1971, working as a general-assignment reporter for the Daily Local News in West Chester, Pennsylvania, near his alma mater, Haverford College. He covered local government and civic events and was promoted to City Editor after about two years. He also started writing a weekly humor column for the paper and began to develop his unique style. He remained at the newspaper through 1974. He then worked briefly as a copy editor at the Associated Press's Philadelphia bureau before joining Burger Associates, a consulting firm.
At Burger, he taught effective writing to business people. In his own words, he "spent nearly eight years trying to get various businesspersons to...stop writing things like 'Enclosed please find the enclosed enclosures,' but...eventually realized that it was hopeless."
In 1981 he wrote a humorous guest column in the Philadelphia Inquirer about watching the birth of his son, which attracted the attention of Gene Weingarten, then an editor of the Miami Herald's Sunday magazine Tropic. Weingarten hired Barry as a humor columnist in 1983. Barry's column was syndicated nationally. Barry won a Pulitzer Prize for Commentary in 1988 for "his consistently effective use of humor as a device for presenting fresh insights into serious concerns."
Barry's first novel, Big Trouble, was published in 1999. The book was adapted into a motion picture directed by Barry Sonnenfeld and starring Tim Allen, Rene Russo, and Patrick Warburton, with a cameo by Barry (deleted in post-production). The movie was originally due for release in September 2001 but was postponed following the September 11, 2001, attacks because the story involved smuggling a nuclear weapon onto an airplane. The film was released in April 2002.
In response to a column in which Barry mocked the cities of Grand Forks, North Dakota, and East Grand Forks, Minnesota, for calling themselves the "Grand Cities", Grand Forks named a sewage pumping station after Barry in January 2002. Barry traveled to Grand Forks for the dedication ceremony.
Articles written by Barry have appeared in publications such as Boating, Home Office Computing, and Reader's Digest, in addition to the Chicken Soup for the Soul inspirational book series. Two of his articles have been included in the Best American Sportswriting series. One of his columns was used as the introduction to the book Pirattitude!: So You Wanna Be a Pirate? Here's How! (ISBN 0-451-21649-0), a follow-up to Barry's role in publicizing International Talk Like a Pirate Day. His books have frequently appeared on the New York Times Best Seller List.
On October 31, 2004, Barry announced that he would be taking an indefinite leave of absence of at least a year from his weekly column to spend more time with his family. In December 2005, Barry said in an interview with Editor and Publisher that he would not resume his weekly column, although he would continue such features as his yearly gift guide, his year-in-review feature, and his blog, as well as an occasional article or column.
In 2005, Barry won the Walter Cronkite Award for Excellence in Journalism.
On Sunday, September 22, 2013, the opening night of the 15th annual Fall for the Book festival in Fairfax, Virginia, Barry was awarded the event's highest honor, the Fairfax Prize, honoring outstanding literary achievement, presented by the Fairfax Library Foundation.
Dave Barry