Billboard country singles chart was his "My First Country Song" (1983) (which also appeared on his Nashville Sessions album), his big country phase actually happened between the years 1969 and 1973. His 1969 version of Merle Haggard's "I Take a Lot of Pride in What I Am" was his final Hot 100 charting single, while his versions of Glen Campbell's "Gentle on My Mind," Marty Robbins' "My Woman, My Woman, My Wife," Bobby Bare's "Detroit City," and Jerry Reed's "Georgia Sunshine" all bubbled under the Hot 100 between 1969 and 1971 (1971 being the year he bowed out of the pop charts for good). This chart activity, though, explains why trade paper op eds expressing worry about certain interlopers sneaking tastes of the country pie would mention his name.
For Martin, dabbling in country was good business sense. By the '70s, the abyss between classic middle-of-the-road vocalists and the pop charts was wider than ever, and country was an acknowledged stepping stone in the era of "cross-country" stations. Although the notion of cross-country seems to be remembered most in terms of country/rock hybridity, it was the MOR/country fusion that had the biggest influence. Country artists such as Charlie Rich, Tammy Wynette, and Ray Price crossed over easily to MOR stations, while MOR artists such as Martin, Bobby Vinton, and Patti Page transitioned almost as easily to country playlists. Martin's own television variety show, as a matter of fact, outlasted competing shows hosted by Johnny Cash and Glen Campbell, and aired into the mid-'70s, when he would also host specials on NBC called Dean Martin Presents Music Country and Music Country USA. (Two of his early seventies films - Something Big (1971) and Showdown (1973) - were westerns.)
This country aspect of Martin's legacy all makes sense in light of early '70s radio and record industry market calibration, but it certainly runs counter to the Rat Pack Dino persona that prevails in the collective memory.
P.S. Dino also had a fullblown country phase in '63 which spawned the albums Country Style and Dean "Tex" Martin Rides Again, but no country hits.
Dean Martin - "My Woman, My Woman, My Wife" (Billboard #110, entered 8/1/70). Written by Marty Robbins. Produced by Jimmy Bowen. 45: "My Woman, My Woman, My Wife"/"Here We Go Again" (Reprise 1970). LP: My Woman, My Woman, My Wife (Reprise 1970).
"An open letter to the women's liberation movement from Dean Martin can be heard on his smash new single," read the copy for a Billboard ad.
Dean Martin - "Detroit City" (1970, Billboard #101, entered 10/31/70; easy listening #36). Written by Denny Dill and Mel Tillis. Produced by Jimmy Bowen. 45: "Detroit City"/"Turn the World Around" (Reprise 1970). LP: My Woman, My Woman, My Wife (Reprise 1970).
Dean Martin's version of "Detroit City" was the fifth and last version of this to hit the Hot 100. Previous interpreters included Bobby Bare (1963), Ben Colder (1963), Tom Jones (1967), and Solomon Burke (1967).
Dean Martin - "Georgia Sunshine" (1971, Billboard #118, entered 1/23/71). Written by Jerry Hubbard. Produced by Jimmy Bowen. Arranged by Ernie Freeman. 45: "Georgia Sunshine"/"For the Good Times" (Reprise 1971). LP: For the Good Times (Reprise 1971).
Dean Martin - "She's a Little Bit Country" (Billboard easy listening #36, entered 5/8/71). Written by Harlan Howard. Produced by Jimmy Bowen. Arranged by Ernie Freeman. 45: "She's a Little Bit Country"/"Raining in My Heart" (Reprise 1970). LP: For the Good Times (Reprise 1970).
Producer Jimmy Bowen and arranger Ernie Freeman went out of their way to keep this composition by Harlan Howard, a stalwart country songwriter, from sounding too much like its title. A later version by George Hamilton IV hit closer to the mark.