[3] The founder, Russ Smith, was a conservative who wrote a long column called "Mugger" in every issue, but did not promote just a right-wing viewpoint in the publication.

The Press touted a Manhattan-focused, controlled distribution system while a good portion of the Village Voice's circulation is outside the NYC metro area.

Smith wrote a column starting with the first issue, which was published under the pseudonym "MUGGER"; it mostly focused on media coverage of politics, as well as restaurant reviews and personal anecdotes.

During Smith's editorship, the Press ran regular columns by the radical Alexander Cockburn; the conservative Taki Theodoracopoulos; Christopher Caldwell, future Weekly Standard editor; Soul Coughing lead singer Mike Doughty (both under his own name and under the pseudonym "Dirty Sanchez"); Adam Mazmanian; Todd Seavey; Paul Lukas; occultist Alan Cabal;[8] Mistress Ruby; J. R. Taylor; Zach Parsi; C. J. Sullivan; Dave Lindsay; Jessica Willis; Spike Vrusho; Ned Vizzini; and Daniel Radosh.

[11] Following the convention established by earlier New York underground papers like East Village Other, New York Press also regularly published cutting-edge comic art, including early work by founding art director Michael Gentile, Kaz, Ben Katchor, Debbie Drechsler, Charles Burns, Mark Beyer, Carol Lay, Mark Newgarden, Ward Sutton, M. Wartella, Gary Panter, Danny Hellman, Tony Millionaire, Ariel Bordeaux and others.

New York Press attracted strong criticism in March 2005 for a cover story entitled "The 52 Funniest Things About the Upcoming Death of the Pope," written by Matt Taibbi.

During Koyen's and Zaitchik's editorship, the paper ran regular columns by Paul Krassner, Michelangelo Signorile, and Matt Taibbi.

In February 2006 all four men resigned from the paper, after the publisher rejected a planned cover story that would have shown the Jyllands-Posten Muhammad cartoons from the controversy in Denmark.

On July 31, 2007, the paper was acquired by Manhattan Media, the owner of Avenue magazine and a small stable of New York community weekly newspapers.

An occasional arts and entertainment critic, and author of the "Slackjaw" column, staff writer Jim Knipfel was one of the paper's mainstays for more than thirteen years.

[19][20] Stephanie Sellars wrote the Lust Life column in 2006–2007, which featured stories about sex from the perspective of a bisexual polyamorist.