Throughout his tenure at Metric, Randy remained in close contact with Lenny Waronker. As Lenny shared with Timothy White in a 1995 Billboard article, it became common for Newman to make a 7 or 8 a.m. phone call to the Waronkers' home, and perform his latest creation live over the phone for Lenny, excitedly discussing its potential. As Lenny's clout at Liberty grew, he, in turn, helped promote Newman's demos to any Liberty artists who would listen, often feeding back suggested song topics to Randy (Lenny reportedly suggested the football theme inspiring "Golden Gridiron Boy").
Through his involvement in song publishing and promotion for Liberty, Waronker soon became a familiar face at two relatively young local record companies: Warner Brothers Records, formed in March 1958 as an adjunct to Jack Warner's successful movie company, and Reprise Records, founded in December 1960 by ex-Capitol Records artist Frank Sinatra. Both record companies were relatively slow in adapting to the pop and rock revolution of the early '60's (Warner Brothers was then best known for its comedic talents, such as Bill Cosby and Bob Newhart; Reprise's first signings included, not surprisingly, Sinatra's aging "Rat Pack" pals Sammy Davis Jr. and Dean Martin).
It made sense then, following Warners' aquisition of Reprise in September 1963, that one priority would be the beefing up of both companies' rock rosters. Though skewed at first towards the softer end of the pop spectrum (the Everly Brothers, Peter Paul and Mary, Trini Lopez), under the guidance of Mo Ostin (Reprise) and Joe Smith (Warners), by the mid- to late-'60's, the two companies had developed reputations for signing on talents both eccentric (the Fugs, Van Dyke Parks, Arlo Guthrie, Ry Cooder) and unique (Jimi Hendrix, Joni Mitchell, Neil Young), most of whom have stood the test of time to be recognized as musical trailblazers.
Waronker's enthusiasm and drive brought him to the attention of Ostin and Reprise A&R chief Jimmy Bowen, who brought Lenny aboard as a junior A&R executive in April 1966. One of his first assignments was to help develop some of the rock-oriented artists acquired that month from the defunct Autumn Records label, which led to his producing the Harpers Bizarre's and Beau Brummels' albums. Newman and Van Dyke Parks were among the writers Lenny brought in to provide some new material for the groups, and it was shortly after the Harpers' landed an FM hit with "Simon Smith" that Ostin recommended to Waronker that they sign Randy on.
Lenny was elated when, on August 15, 1967, his best friend officially joined the Reprise roster and began work on his own debut album.