Since 1957 the Milwaukee Press Club has honored Wisconsin leaders each year with its Headliner award. The list of winners is a who's who of Wisconsin greats – from the worlds of politics, business, sports, religion, entertainment and the media. The Headliner award is presented each spring at the Gridiron banquet, which also honors winners of the club's Excellence in Wisconsin Journalism competition and a Sacred Cat. The Press Club's board of governors and the Gridiron Committee collaborate in the selection of a Headliner.

Honorees

• 2011 - Sue Dragisic, Marty Kaiser
• 2010 - Will Allen, Kitty Brennan
• 2009 - Michael Grebe, Gwen Jackson
• 2008 - Bob Harlan, Joseph Zilber
• 2007 - Sheldon Lubar
• 2006 - Bob Reitman, Sister Joel Read
• 2005 - Michael Cudahy
• 2004 - Dr. Zorba Paster, Tom Clark
• 2002 - Tom Crean, Bruce Pearl
• 2001 - Russell Bowman, Christopher Goldsmith, Jack Pelisek
• 2000 - Andreas Delfs
• 1999 - Roger Fitzsimonds
• 1998 - Janine Geske
• 1997 - Jacquelyn Mitchard
• 1996 - Mike Holmgren
• 1995 - Allen H. Selig
• 1994 - Pat Richter, Bonnie Blair and Dan Jansen
• 1993 - Jane and Lloyd Pettit
• 1992 - Howard Fuller
• 1991 - Les Aspin
• 1990 - Lindy Infante
• 1989 - Mitchell Fromstein
• 1988 - T. Michael Brophy
• 1987 - Archbishop Rembert Weakland
• 1986 - Charles McNeer
• 1985 - Ben Marcus and Stephen H. Marcus
• 1984 - Paul E. Hassett
• 1983 - Ben Barkin
• 1982 - Max Karl
• 1981 - Albert A. Silverman
• 1980 - Catherine B. Cleary
• 1979 - Allen H Selig
• 1978 - Harry C. Bockel
• 1977 - Warren P. Knowles
• 1976 - Robert V. Krikorian
• 1975 - Arnold D. K. Mason
• 1974 - Rev. John P. Raynor, S.J.
• 1973 - Francis E. Ferguson
• 1972 - Norman N. Gill
• 1971 - Mrs. Harry Lynde Bradley and Donald C. Slichter
• 1970 - Hazel Maxwell and Harold Morgan
• 1969 - James A. Lovell
• 1968 - George A. Parkinson
• 1967 - Howard J. Tobin
• 1966 - Walter H. Bender
• 1965 - Robert A. Uihlein, Jr.
• 1964 - Leo Tiefenthaler
• 1963 - Irwin Maier
• 1962 - Albert S. Puelicher
• 1961 - Eliot Fitch
• 1960 - S. Lloyd Niemeyer
• 1959 - Edmund Fitzgerald
• 1958 - George F. Kasten
• 1957 - Harold S. Vincent