Fancy Dancing (2002)

Thirty year old Torontonian Asa Gemmill loves movie musicals of the 1930s and 1940s, especially little known Canadian movies starring Mar Stoddart, who he views as the Canadian Fred Astaire, and his regular partner Doreen Gaynor, most specifically one called "Fancy Dancing". He is irresponsible in the way he lives his life - living in the seedy Winchester Hotel where Stoddart once performed and where they still play big band and jazz standards, rooming with a fellow Scot named Schiff who is only understandable with subtitles, sleeping during the day, and trying to bed all the hotel club's aspiring Doreen Gaynors at night - at least in the eyes of his ex-wife, Charity, who he still loves. Charity threatens to cut off his access to their infant son Michael unless he gets his act together. Through an intervention, Asa ends up going to work at his Uncle Billy's small advertising agency. Although the nine to five life isn't for him, which isn't helped working under the supervision of anal Nat Porter, Asa may gain that focus in life that he needs with the help of the agency's slightly off-kilter art director, Karen.