This pairing takes a long, serious look at the perils of alcoholism, with two classic films. Starting off, it's the first film to have the same individual win the Academy Awards for Best Director and Best Screenplay for the same project. In writer/director Billy Wilder's "The Lost Weekend," from 1945, we're introduced to writer Don Birnam (Ray Milland, who also won the Academy Award for Best Actor for this film) who is getting ready to leave for a long weekend of writing on a farm out in the middle of nowhere. His brother, Wick (Phillip Terry) is going with him, and has taken great pains to make sure that Don is taking no alcohol with him, as Don is an alcoholic. Don's girlfriend, Helen St. James (Jane Wyman) stops in to encourage him and send him off with a few small gifts. All the while, Don is desperately trying to get a bottle of whiskey he's hung out his window on a string into his luggage without Wick or Helen seeing him. After Wick discovers the bottle and dumps it out, they both depart, leaving Don frantically searching his apartment for one of the other bottles he's hidden... to no avail: Wick has found them all and disposed of them. But the arrival of their cleaning lady tips Don off to a ten-dollar bill she's supposed to receive for her work. Instead, Don lies about finding it and, after she departs, heads off to the liquor store, and then the bar. There, he's served and admonished by bartender Nat (Howard Da Silva), and flirted with by local call girl Gloria (Doris Dowling). This begins a booze-fueled spiral that might just be terminal, depending on Don's choices and Helen's commitment. Also starring Frank Faylen, Anite Sharp-Bolster, and Frank Orth.