April 13, 1988 – The first issue of New York Press appears, just a few weeks after the first issue of Seven Days, another weekly publication launched by The Village Voice. Russ Smith, formerly of the Baltimore City Paper, is the Press first editor, and part owner. The offices of the Press are located at 530 Broadway at Spring St.
1988 – Work by cartoonists Ben Katchor (Julius Knipl, Real Estate Photographer) and Charles Burns (Big Baby) appears in the first and third issue, respectively.
September 30, 1988 – First Best of Manhattan edition is published. Includes Best 24-Hour Copy Shop (At 3 oclock in the morning we like to watch acid-addled Axl Rose wannabees try to spell the names of their bands on flyers.), Best Buy for 50 cents (The Wall Street Journal), Best Short Circuit of Political Career (Al Gore & Ed Koch) and Best Place to be Treated Like Shit (The Corner Bistro).
January 6, 1989 – Phyllis Orrick moves to New York from Baltimore to become associate editor of the Press.
August 1989 – The Press moves into the former offices of Spy magazine in the Puck Building at Houston and Lafayette. In its Aug. 25 issue, the Press publishes PUCK: A History of a House of Mirth, Home of Americas First Humor Magazine by Phyllis Orrick.
April 1990 – John Strausbaugh moves from Baltimore and becomes associate editor.
September 1990 – Sam Sifton does not move to New York from Baltimore, but he is nevertheless hired as restaurant reviewer.
1990 – Seven Days folds.
1991 – M. Doughty, later of the band Soul Coughing, begins writing music reviews, along with J.R. Taylor. Doughty later publishes pieces under the pseudonym Dirty Sanchez.
1992 – Sam Sifton joins the Press staff as a full-time writer.
1993 – Jim Knipfels Slackjaw column first appears. Soon afterward, he is hired as the Press receptionist.
1993 – William Monahan, a 33-year-old writer and former musician, begins publishing essays and restaurant reviews. He left in 1995 and later won the Academy Award for his screenplay adaptation of The Departed.
1995 – Jonathan Ames begins a first-person column in the Press; his columns later appear in successful collections published by Scribner.
February 1996 – Village Voice, previously $1.25 per issue, begins free distribution.
May 1996 – Amy Sohns first story, Blow-Up Boyfriend appears in late May 1996 in a section called First Person. By June 1996 she has been given a weekly sex column called Female Trouble.
May 1997 – Armond White is hired as film critic for the paper. His first reviews are of Gregg Arakis Nowhere and Luc Bessons The Fifth Element. He calls Besson le hack Franais and says he is often mistaken as a French Spielberg.
1997 – The Press moves to 333 7th Avenue, also the home of a Board of Education rubber room, at West 28th Street, across from Mustang Sallys.
January 1997 – John Strausbaugh discovers the work of Stuyvesant High School student Ned Vizzini and gives him a column while still in school. Vizzini has since published two novels.
1998 – Sam Sifton leaves the paper, hired by Tina Brown to join Talk magazine. He later joins The New York Times, where he now serves as cultural editor.
August 1999 – Amy Sohn leaves to join New York magazine as its sex columnist.
2002 – Russ Smith sells the Press to Avalon Equity Partners, which also publishes The New York Blade. John Strausbaugh leaves the paper to become a full-time author; Lisa Kearns, the papers managing editor, is named editor in chief.
2002 – Armond White, continuing his vocal support for struggling movie director Steven Spielberg, chooses A.I. as one of the 10 best movies of all time.
2003 – Jeff Koyen, former Press production editor, is named editor in chief.
2003 – After serving as the sports editor of The Moscow Times and creating the Buffalo-based magazine The Beast, Matt Taibbi begins writing a regular political column for the Press.
March 2003 – First 50 Most Loathsome New Yorkers edition published.
2003 – Avalon launches New York Sports Express, which folds the following year.
March 2005 – Matt Taibbi publishes a cover story, The 52 Funniest Things About the Upcoming Death of the Pope, that causes politicians to rail against the Press and drives advertisers away. Shortly afterward, editor Koyen quits after a suspension; Taibbi follows him out the door and joins Rolling Stone as a contributing editor.
April 2005 – Alexander Zaitchik, Koyens deputy, is named editor in chief.
August 2005 – Zaitchik quits the Press and moves to Moscow. Harry Siegel, a conservative former editorial writer at The New York Sun, is named editor in chief on the recommendation of former editor Russ Smith. Siegel hires sportswriter Tim Marchman, now at The Sun, and political reporter Azi Pazbarah, now at The New York Observer.
February 7, 2006 – Siegel and three other editors resign over thwarted plans to reprint controversial Mohammed cartoons from a Danish newspaper.
February 8, 2006 – Steve Weinstein, former editor of Press sister publication The New York Blade, is named interim editor.
April 2006 – Adario Strange is named editor. He worked previously as editor of The Source.
June 2006 – Strange fires Jim Knipfel after 13 years at the Press. He hires former mayor Ed Koch as columnist and launches Hype Stalker column.
April 2007 – Strange leaves the Press to resume his filmmaking career. Jerry Portwood, the Press arts editor, is named editor in chief.
August 2007 – Manhattan Media, owner of West Side Spirit, Avenue, New York Family and other publications, buys the Press. President Tom Allon immediately eliminates sex advertising. The Press moves east to 79 Madison Avenue at 28th Street, across from Dunkin Donuts and the Carlton Hotel.
September 2007 – David Blum, former editor in chief of The Village Voice, is named editor in chief of the Press.
April 2008 – The Press publishes My Wall Street Journal, a parody edited by Tony Hendra with writers from SNL, The Daily Show, Monty Python and The Onion.