Since Errol Flynn was a Warner Bros. star and TCM is part of the Time Warner mega-conglomerate (and before that, Turner owned the rights to the WB library up to 1948), Flynn flicks have a been a TCM staple from the get-go.
Flynn did star in some movies in the 1950s that are really hard to find – e.g., Adventures of Captain Fabian (1951), Lilacs in the Spring (1954), and King’s Rhapsody (1954) – but those will remain hard to find as TCM isn’t presenting any of them.
Instead, you’ll have the chance to see (once again, most likely) Flynn in his Warners heyday, in vehicles such as Gentleman Jim (1942), The Prince and the Pauper (1937), and San Antonio (1946).
The best of the Flynn movies being shown on TCM is, of course, Michael Curtiz and William Keighley’s The Adventures of Robin Hood (1938), the only entry on Flynn Day featuring the actor’s most frequent leading lady, Olivia de Havilland. If you haven’t watched it 100 times already (it’s always on), then perhaps here’s your chance.
Else, I’d recommend Curtiz’s Virginia City partly because the underrated Miriam Hopkins is in it; partly because it has a solid first hour.
Frank Borzage’s Green Light (1937), about idealism and self-sacrifice, is also worth a look because it’s so godawfully well-intentioned it must be seen to be believed.
I still haven’t watched Lewis Milestone’s Edge of Darkness, but it’s supposed to be a solid World War II drama. Robert Rossen, whose All the King’s Men would win the 1949 Best Picture Oscar, penned the screenplay based on William Woods’ novel about anti-Nazi Norwegian fighters. Ann Sheridan is another good reason to check this one out. The capable supporting cast includes Walter Huston, Helmut Dantine, Ruth Gordon, Judith Anderson, John Beal, and Nancy Coleman.
Schedule and synopses from the TCM website:
3:00 AM Virginia City (1940)
A rebel spy poses as a wild West dance hall girl. Cast: Errol Flynn, Miriam Hopkins, Humphrey Bogart. Dir.: Michael Curtiz. Black and white. 121 min.
5:02 AM Short Film: Visiting Virginia (1947)
In this “Traveltalk,” we learn about the agriculture, history, and natural wonders of Virginia. Cast: James A. Fitzpatrick C-9 min.
5:15 AM San Antonio (1945)
A reformed rustler tracks down a band of cattle thieves and tries to reform a crooked dance-hall girl. Cast: Errol Flynn, Alexis Smith, S.Z. Sakall. Dir.: David Butler. Color. 109 min.
7:15 AM Uncertain Glory (1944)
A French playboy gets serious when his country is threatened during World War II. Cast: Errol Flynn, Paul Lukas, Lucile Watson. Dir.: Raoul Walsh. Black and white. 102 min.
9:00 AM Objective, Burma! (1945)
An American platoon parachutes into Burma to take out a strategic Japanese outpost. Cast: Errol Flynn, George Tobias, Henry Hull. Dir.: Raoul Walsh. Black and white. 142 min.
11:30 AM Prince And The Pauper, The (1937)
Rousing adaptation of the Mark Twain tale of a 16th-century prince who trades places with a lookalike peasant. Cast: Errol Flynn, Claude Rains, Billy and Bobby Mauch. Dir.: William Keighley. Black and white. 118 min.
1:45 PM Adventures of Errol Flynn, The (2005)
Documentary that chronicles the life and career of swashbuckler Errol Flynn. Black and white. 87 mins
3:15 PM Adventures of Robin Hood, The (1938)
The bandit king of Sherwood Forest leads his Merry Men in a battle against the corrupt Prince John. Cast: Errol Flynn, Olivia de Havilland, Basil Rathbone. Dir.: William Keighley, Michael Curtiz. Color. 102 min.
5:00 PM Sea Hawk, The (1940)
A British buccaneer holds the Spanish fleet at bay with the covert approval of Elizabeth I. Cast: Errol Flynn, Claude Rains, Flora Robson. Dir.: Michael Curtiz. Black and white. 128 min.
7:15 PM Adventures of Don Juan (1948)
The legendary lover saves his queen from treason. Cast: Errol Flynn, Viveca Lindfors, Alan Hale. Dir.: Vincent Sherman. Color. 111 min.
9:15 PM Gentleman Jim (1942)
Fanciful biography of 19th-century boxing champion Jim Corbett. Cast: Errol Flynn, Alexis Smith, Ward Bond. Dir.: Raoul Walsh. Black and white. 104 min.
11:15 PM Edge Of Darkness (1943)
Resistance fighters battle the Nazis in occupied Norway. Cast: Errol Flynn, Ann Sheridan, Walter Huston. Dir.: Lewis Milestone. Black and white. 119 min.
1:30 AM Green Light (1937)
An idealistic doctor sacrifices his career to protect an elderly surgeon. Cast: Errol Flynn, Anita Louise, Cedric Hardwicke. Dir.: Frank Borzage. Black and white. 85 min.
Turner Classic Movies website.