Superman and The Gipper

In 1940, Ronald Reagan played the part of the ill-fated football player George Gipp, whose nickname was "The Gipper" in Knute Rockne All American.  Pat O'Brien played the title role.  The movie was distributed by Warner Bros.

In an uncredited role, future Superman actor George Reeves played a distraught player on Rockne's team.

To date, I have not seen any stills from this movie showing Reagan and Reeves together.  I did manage to make the below screen capture of a scene from the movie showing both Reagan and Reeves.

It was due to this movie that Reagan also became known as "The Gipper."

Above, Ronald Reagan as George Gipp talks with Pat O'Brien as Knute Rockne.
In the background at right, is actor George Reeves (circled).

Reagan didn't just only meet one Superman, here's another one as this White House photo shows:

Above, Christopher Reeve and President Reagan at the White House.