There was pressure on the band to move quickly and to save time they began reworking old tunes. One of Tom Johnston's songs, "Osborn", had been an improvisational piece that the band played live. After laying down the track, according to producer Ted Templeman. "We still really didn't have it, and I said, 'Make it about a train, since you have this thing about "Miss Lucy down along the track." So he came up with "Long Train Runnin'."
Synthesizers and strings were brought in to record The Captain and Me. Synth programmers Malcolm Cecil and Robert Margouleff were brought in to engineer the opening track, "Natural Thing". Striving for a synthesized sound like that of The Beatles' "Being for the Benefit of Mr. Kite!" they would overdub individual notes to create chords for the song's bridge.
"Dark Eyed Cajun Woman" was a bluesy track (one of the band's earliest) and seen by Johnston as a tribute to the blues and B.B. King. "South City Midnight Lady", while being about San Jose, is not about any woman in particular. Jeff Baxter of Steely Dan played pedal steel guitar on the track. He would become an official Doobie Brother in 1974. Cecil and Margouleff also added the synthesized effect of a woman whispering at the end.
"Clear as the Driven Snow", according to Johnston, is a warning about recreational chemical abuse, which reflected the band members' lifestyles at that time.
The second side of the album opens with the rocker "Without You". This song, like many others, had begun as a jam. "That song had both drummers playing at the same time," Johnston stated. "It was kind of a tribute to The Who. We did it in concert for quite a while."
Patrick Simmons' short solo guitar piece "Busted Down Around O'Connelley Corners" segues into "Ukiah", which Johnston wrote in tribute to the area. Johnston said, "We played a few shows in Ukiah, and I used to camp out a lot in the area when I was going to college." The song's back-to-the-land sentiments also reflected some of his feelings at the time, although he admitted he probably couldn't make it as a farmer. This track segues into the album closer and title track, "The Captain and Me". According to Johnston, the captain is no one in particular and the lyrics were written at the last minute and have no real meaning. The song was released as a single in the Netherlands and received some airplay there.
The artwork found on the front and back of the album features the band, including manager Bruce Cohn, dressed in 19th century western garments and riding a horse-drawn stagecoach beneath an unfinished modern freeway overpass. "All that stuff came from the Warner Bros. film studios lot," Tom Johnston said. "It must've been a lot of work for the guys who brought up the horse team and the carriage and the clothes. It was fun to do - they had coffins out there, all kinds of crazy stuff." The photography was done by Michael and Jill Maggid. The setting for the cover was located at the Newhall Pass interchange of the Interstate 5 and California State Route 14 freeways near Sylmar, California that collapsed during the 1971 San Fernando earthquake. This same section of freeway would collapse again during the 1994 Northridge earthquake.
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