If I Knew Then (What I Know Now) is a 1939 song written by Dick Jurgens and Eddy Howard and originally performed by Jurgens' big band with Eddie Howard on vocal. It was first recorded on August 19, 1939 and released as a single that same year, landing in the big band pop/jazz territory of the Swing era. The lyrics express regret and the idea of wishing to know now what one wished they knew then. The tune charted briefly in 1939 and has since been covered by many artists, including Bing Crosby with John Scott Trotter and His Orchestra in 1940, Johnny Mercer and his Pied Pipers in 1945, Sammy Kaye, Sarah Vaughan on her album Sarah Vaughan with Clifford Brown and Swingin' Easy, and Ray Conniff whose version bubbled under the Hot 100, reaching No 26. It has appeared on various albums and collections over the years, with later renditions by artists such as The Four Freshmen in 1961 and even a 2019 scat version by Jeff Goldblum and The Mildred Snitzer Orchestra.
