Two notable films have been made about the transition from silent film to talkies, Singin' in the Rain is the funniest (if not simply just because the other film is Sunset Boulevard) it is frequently referred to as the best musical of all-time and sits at number five on the AFI top one-hundred films lists.
Don Lockwood's motto is "Dignity, always dignity." Just don't ask the matinee idol about how he started in Hollywood and that motto will stand true. He along with his best pal/songman Cosmo Brown (Donald O'Connor) have hit it big and are enjoying their Hollywood lifestyles. Currently Don is linked to his frequent co-star Lina Lamont (Jean Hagen) but in truth he can't stand her and she is too dumb to know the difference.
Talkies are ushering in a new age of film and even people like aspiring actress Kathy Selden (Debbie Reynolds) are starting to take notice. Don's latest picture The Duelling Cavalier is going to be transformed into a talkie, but you guessed it, Lina's voice simply won't allow that picture to succeed. With the help of Kathy, Cosmo suggests they turn the Duelling Cavalier into the Singing Cavalier. Kathy and Don soon fall in love, but all the work they have put into The Singing Cavalier is endangered when Lina learns her role has been recorded over and threatens to blow the situation sky-high for all of them.
Although it is the first meta-film to really send up Hollywood what really made Singin' in the Rain the greatest musical of its time is in the fashion the music blends seamlessly with the plot. Nothing is shoe-horned in just for the sake of having a song. And what makes the film one of the best comedies is the rich dialogue that should be savored after every line. As Lina is lamenting about Don's barbs regarding her stupidity she counters, "Sticks and stones may break my bones..." to which Don replies, "I'd like to break every bone in your body." You just don't get one-liners like that in film anymore.