Ray Enright
Ray Enright( March 25, 1896 – April 3, 1965) was an American film director.
He directed 73 films between 1927 – 53, many of them for Warner Bros.
He oversaw comedy films like Joe E. Brown vehicles, and five of the six informal pairings of Joan Blondell and Glenda Farrell.
Enright was born in Anderson, Indiana, and died in Hollywood, California, from a heart attack.
Rob Shuter
Naughty But Nice Rob( born Robert James Shuter on 16 July 1973, in Birmingham, United Kingdom) is a gossip columnist, magazine editor, talk- show host, and author.
Naughty but Nice (1939 film)
Naughty but Nice is a 1939 Warner Bros. musical comedy film directed by Ray Enright, starring Dick Powell and Ann Sheridan and featuring Gale Page, Ronald Reagan, and Helen Broderick, with Allen Jenkins, ZaSu Pitts, and Maxie Rosenbloom in supporting roles.
The original story and screenplay were written by Richard Macaulay and Jerry Wald, and the film includes songs with music by Harry Warren and lyrics by Johnny Mercer, as well as music adapted from Bach, Beethoven, Liszt, Mozart, Robert Schumann, and Wagner.
Ann Sheridan did her own singing in the film, except for song" In a Moment of Weakness", in which she was dubbed by Vera Van.
Mickey the Kid
Mickey the Kid is a 1939 film.
It was directed by Arthur Lubin.
The Counter Jumper
The Counter Jumper is a 1922 American film directed by Larry Semon and featuring Oliver Hardy.
It is a remake of the 1919 film" The Grocery Clerk", which was also directed by Semon.
The film was screened at the Museum of Modern Art in 2009 as part of a series examining slapstick.
The Grocery Clerk
The Grocery Clerk is a 1919 American silent short comedy film directed by and starring Larry Semon, Lucille Carlisle, Monty Banks, Frank Hayes, Frank Alexander, Pete Gordon, and Jack Duffy.
The film has been released as part of a collection on DVD.
Larry Semon
Lawrence "Larry" Semon (February 9, 1889 – October 8, 1928) was an American actor, director, producer, and screenwriter during the silent film era.
In his day, Semon was considered a major movie comedian, but he is now remembered mainly for working with both Stan Laurel and Oliver Hardy before they started working together.
He is also sometimes noted for directing (as well as appearing in) the 1925 silent film "The Wizard of Oz", which had a slight influence on the better-known 1939 talkie "The Wizard of Oz" released by MGM.
The film was included in the 2005 three-disc DVD version of the 1939 film, along with other silent "Oz" movies.
Panama Lady
Panama Lady is a 1939 film starring Lucille Ball.
King of the Turf
King of the Turf is a 1939 film drama starring Adolphe Menjou.
Naughty But Nice (1927 film)
Naughty But Nice is a 1927 silent American comedy film.
Colleen Moore plays Bernice Sumners, a hayseed sent to a ritzy boarding school for finishing after her family strikes it rich in oil.

Question: Which film has the director died earlier, The Grocery Clerk or Naughty But Nice (1939 Film)?
Answer: The Grocery Clerk