From my magazine (historical) related collection:

• The Madison Square Garden boxing program dated February 12, 1965 (50¢). My brother and I went to see Rubin "Hurricane" Carter fight Luis Rodriguez in a 10 rounder (Rodriguez won). (It was a year later that Carter was charged with the death of two people in a bar and was immortalized in a song by Bob Dylan). The program was signed by Rocky Graziano (on the cover) who was sitting near us and by Emile Griffith (inside under a picture of him fighting Luis Rodriguez) - Griffith wrote "My Best Fight - Emile Griffith".
• The May, 1969 issue of "Sport" magazine comemorating 100 years of baseball (50¢).
• 20th Annual Anniversary issue of "Playboy"; Jan 1974, $1.50
• 25th Annual Anniversary issue of "Playboy"; Jan 1979, $3.00
• 30th Annual Anniversary issue of "Playboy"; Jan 1984, $4.00
• 35th Annual Anniversary issue of "Playboy"; Jan 1989, $5.00
• 40th Annual Anniversary issue of "Playboy"; Jan 1994, $5.95
• 50th Annual Anniversary issue of "Playboy"; Jan 2004, $7.99
• 40th Anniversary Celebration of "Esquire"; Oct 1973, $2.00; a truly colossal edition of over 500 pages containing works by the likes of Hemingway, F. Scott Fitzgerald, Steinbeck, Nabokov, Talese, Truman Capote, James Baldwin, Thomas Wolfe and Huxley.
• "Time" magazine dated June 23, 1975 (75¢) with cover story on the movie opening of "Jaws".
• "Time" magazine issues dated July 4, 1776 (really 1976) and Sept. 29, 1789 (really 1976) ($1.00 each); they were special bicentennial issues with Thomas Jefferson and George Washington on their respective covers. Both issues reported on stories and events of their day. (Very interesting for history buffs).
• "Time" magazine dated August 25, 2003 ($3.95) reporting on the cover story about the great northeast blackout.

I have MANY newspaper copies collected as well.