[9] For most of its history, the Club bylaws excluded women from becoming members or even guests at its annual dinner.

[10][11] Although the National Press Club began admitting women in 1971, the Gridiron was reluctant to follow suit.

[12] Eventually, the club began expanding beyond print journalism to include media figures such as Tim Russert of NBC News, Bob Schieffer of CBS News, Mara Liasson of National Public Radio, and Judy Woodruff of PBS.

The skits and speeches by the politicians are expected to "singe not burn", be self-deprecating or otherwise sharply comedic.

[23] In 2017, the Gridiron Club and Foundation's annual show sold up to five tickets to the National Press Club members at $70 each, held 5 March 2017 in the Washington Renaissance Hotel, 999 Ninth Street NW, with a reception that began at 2 p.m. and the reprise (show) that began at 3 p.m. and ended at 5 p.m.[24] It claims to offer a neutral ground on which political operatives, members of the press and elected officials can break bread together.

[9] The Gridiron Club Dinner has been subject to criticism that it encourages journalists to engage in undue coziness with the political officials they are supposed to fairly cover, and also that the public spectacle of "playing footsie" with reporters' main subjects is bringing the political press into disgrace.

In 1970, after the press's "sophomoric" skits Richard Nixon and Spiro Agnew performed Dixie to the ire of the one black attendee.

[31][32] Proof of vaccination was required for entry, and no cases of serious illness were reported as resulting from the dinner.