Which recipient of the US Congressional Gold Medal won an Oscar nomination as a film director and also had a number one hit on the Billbaord chart?

Just a guess Frank Sinatra?

Harry Chapin?

Yes, it is Harry Chapin. The film he made was 'Legendary Champions' (1968) about World Heavyweight Boxing Champions (actually the first part of what was originally intended as a trilogy). The No. 1 song was 'Cats in the Cradle'. The Congressional Medal was awared after his death to his widow, Sandy, and commemorated at a special Carnegie Hall celebration where a host of stars performed for Harry, the humanitarian (Bruce Springsteen, Graham Nash, Harry Belafonte, Pat Benatar and Judy Collins among many others).
Good answer bab. And mozart - well Franck did everything else didn't he?

"Legendary Champions" was directed by Chapin, but he did not get a nomination for Best Director for it. The film was nominated for "Best Docmentary, Features", but that award generally is awarded to the producer, in this case, William Clayton.

http://imdb.com/title/tt0063222/awards

Chapin's page on imdb.com - http://imdb.com/name/nm0152166/

Clayton's page on imdb.com - http://imdb.com/name/nm0147326/