Catch 22 is about the Italian Campaign. It features a USAAC medium bomber unit based in Italy that bombs targets in Northern Italy in support of the 15th Army Group. It covers many of the common experiences of servicemen in Italy, including their relations with the local population. Catch 22 captures the insanity of war the FUBARS and lunacy of that great oxymoron "Military logic". The Italian campaign embodies all of that lunacy from the strategic disagreement between the allies about the campaign, to the rationale for any operations in a side show - a distraction whose main military purpose was to distract the Germans from efforts on other fronts. Here is a great truth
In the movie is it possible they were supposed to be in Sicily like they talk about that one pilot bailing out and paddling the wrong direction always toward southern France and at the end arkin takes a raft and starts paddling out to sea
"Patton", while not exclusively about the Italian campaign, does address the Sicilian portion of the campaign.
"Force of Arms"-1951-William Holden "The Story of G.I. Joe"-1945-Robert Mitchum--Interesting one here, it was based on stories written by War Correspondent Ernie Pyle (played by Burgess Meredith in the film). Ernie Pyle was involved in the making of the film, but never saw it. He was killed on Ie Shima two months before it premiered. "Go For Broke"-1951-Van Johnson Three good movies related to the Italian Campaign.