"If I Knew Then (What I Know Now)" is a 1939 song written by Dick Jurgens and Eddy Howard. The original recording was made by Dick Jurgens and His Orchestra, with Eddie Howard on vocal, on 19 August 1939. It was issued as a 78 rpm single on the Conqueror label (catalogue number 9303), coupled with "Lilacs In The Rain", and it charted briefly in 1939. The original is classed in the jazz and pop genres, in the big band style.
Later versions include a recording by Bing Crosby, made on 9 February 1940 with John Scott Trotter and His Orchestra, and one by Johnny Mercer and the Pied Pipers in 1945. Sammy Kaye and His Orchestra and Sarah Vaughan also recorded the song, as did The Four Freshmen in 1961 and Val Doonican in 1968. Ray Conniff's version bubbled under the Billboard Hot 100, with a peak at No. 26. In 2019 Jeff Goldblum recorded an instrumental scat version with The Mildred Snitzer Orchestra.
