Four TLSs and a photo signed by composer Stephen Sondheim: the four typed letters, each signed either “Stephen,” “Stephen S.,” or with his full name, each one page, 5.75 x 7.75 personal letterhead, all addressed to film historian and television presenter Robert Osborne, dated between 1995 and 2010. Highlights include: October 12, 1995: “Perhaps some time in the future we can challenge each other with movie trivia"; March 3, 1997: “Thanks for continuing to send the TCM schedules”; December 18, 2008: “In your introduction to ‘Payment Deferred,’ which I saw last week, you said that Charles Laughton didn’t get along with Maureen O’Sullivan because he wanted Elsa Lanchester to play the part”; and February 25, 2010: “I hate to look a gift horse in the mouth, but the enclosed is flawed. Any time you can get another copy, I would—as always—be grateful.” Also included is a satin-finish 10 x 8 photo of Sondheim in a pleasant up-close pose, signed and inscribed in black felt tip, “To Bob—‘Affectionately yours,’ Steve.” In overall fine condition, with a trivial ding to right of photo. Accompanied by three original mailing envelopes. Robert Osborne (1932-2017) was best known for more than twenty years as the primary host of the cable channel Turner Classic Movies. Prior to TCM, Osborne had been a host on The Movie Channel, and then earlier as a columnist for The Hollywood Reporter.