The Yankee Señor
The Yankee Señor is a 1926 American silent western film directed by Emmett J. Flynn and starring Tom Mix, Olive Borden and Margaret Livingston.
Steven Brill (filmmaker)
Steven Brill( born May 27, 1962) is an American actor, film producer, director, and screenwriter.
He directed and co-wrote" Little Nicky" and directed" Mr. Deeds Without A PaddleHeavyweights", and" Drillbit Taylor".
He has had cameo roles in all three" Mighty Ducks" movies, and appeared in" The Wedding Singer Mr. Deeds" and" Knocked Up", although his role in the latter has been miscredited to Judd Apatow.
He also appeared as the Barfly in" Sex, Lies, and Videotape".
As a director, Brill was one of the central players( alongside Harvey Weinstein) in the 2007/2008" Fanboys" reshoot/ editing controversy.
Logan Sandler
Logan Sandler is an American writer and director who is best known for his first feature film" Live Cargo".
Race for the Yankee Zephyr
Race for the Yankee Zephyr( also known as Treasure of the Yankee Zephyr) is a 1981 New Zealand suspense – action – thriller film directed by David Hemmings and starring Ken Wahl, Lesley Ann Warren, George Peppard and Donald Pleasence.
Emmett J. Flynn
Emmett J. Flynn( November 9, 1892 in Denver, Colorado – June 4, 1937 in Hollywood, California) was an American director, screenwriter, actor, and producer.
Ben Palmer
Ben Palmer is a British film and television director who is known for being the director of" Bo' Selecta" and" The Inbetweeners".
Little Nicky
Little Nicky is a 2000 American fantasy comedy film directed by Steven Brill.
It stars Adam Sandler as Nicky Schear, one of Satan's three sons as he attempts to save his father and prevent his brothers from taking over Earth.
The film was a financial failure and received negative reviews from critics.
Dan Milne
Dan Milne is a British actor/ director who is possibly best known for his role in" EastEnders".
Elliot Silverstein
Elliot Silverstein( born August 3, 1927, in Boston, Massachusetts) is an American director, who is best known for being the director of the movie" Cat Ballou"( 1965).
Scotty Fox
Scott Fox is a pornographic film director who is a member of the AVN Hall of Fame.

Question: Which film has the director who is older than the other, Little Nicky or The Yankee Señor? 
Answer: The Yankee Señor