Ask "Mr. Music"
Jerry Osborne

Now in our 29th year (1986-2015) — Over 2,900 Questions Answered
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DEAR JERRY: I'm hoping you can identify the singer and song played at the end of the April 26th episode of Mad Men, titled "Time and Money."

All I know is that it's about Don Draper having or not having money in his pocket.
—Arlene Rogers, Sonoma, Calif.

DEAR ARLENE: Most Mad Men episodes conclude with a recording from the 1950s or '60s, and as often as not it will be something unfamiliar to the average viewer. I say this based on the many inquiries over the years that are similar to yours.

"Time and Life" (not "Time and Money") is number 11 of 14 episodes in the final season of this acclaimed series.

Accompanying the fade-to-black and rolling credits is Dean Martin's "Money Burns a Hole in My Pocket," a Top 30 single in the summer of 1954.

Both this tune and its flip side, "Sway (Quien Sera)" (Capitol 2818) are heard in the 1954 Martin and Lewis Paramount picture, "Living It Up."

As an aside, the film sequences for "Money Burns a Hole in My Pocket" and "Ev'ry Streets a Boulevard in Old New York" are regarded as among the most entertaining ones found in 1950s musical comedies.

DEAR JERRY: I know there are some country stars who occasionally recorded duets with other artists. A few, and Willie Nelson comes to mind, had No. 1 hits with several different artists.

I don't think this is nearly as common among pop-rock artists.

For example, does anyone rank above Paul McCartney when it comes to having No. 1 hits as half of a duet?

Also, we know about Frank and Nancy Sinatra, but what other duets comprised of relatives had No. 1 hits?
—Josh Wilburn, Raleigh, N.C.

DEAR JOSH: Sir Paul topped the charts three times, first when teamed with Linda McCartney (1971 - "Uncle Albert/Admiral Halsey"), then Stevie Wonder (1982 - "Ebony and Ivory"), and Michael Jackson (1982 - "Say Say Say").

He nearly had four, but "The Girl Is Mine," also with Jackson in 1982, peaked at No. 2.

No one in the pop field had more singing partners in this category than Paul McCartney; however, Jo Stafford is his equal as she also reached No. 1 with three different duet friends: Johnny Mercer (1945 - "Candy"); Red Ingle & the Natural Seven with Jo Stafford performing as Cinderella G. Stump (1947 - "Temptation [Tim-Tayshun])"; and Gordon MacRae (1948 - "My Darling, My Darling").

There are four runners up, each of whom reached No. 1 with two different duet partners:

Elton John: with Kiki Dee (1976 - "Don't Go Breaking My Heart") and George Michael (1991 - "Don't Let the Sun Go Down on Me")
Bill Medley: as the Righteous Brothers with Bobby Hatfield (1965 - "You've Lost That Lovin' Feelin'" and 1966 - "[You're My] Soul and Inspiration") and Jennifer Warnes (1987 - "[I've Had] The Time of My Life")
Barbra Streisand: with Neil Diamond (1978 - "You Don't Bring Me Flowers") and Donna Summer (1979 - "No More Tears [Enough Is Enough]")
Jennifer Warnes: with Joe Cocker (1982 - "Up Where We Belong") and Bill Medley (1987 - "[I've Had] The Time of My Life")

Since you chose Willie Nelson as the standard for comparison, these six different duet partners accounted for eight of his No. 1 country hits:

Waylon Jennings (1975 - "Good Hearted Woman"; 1978 - "Mammas Don't Let Your Babies Grow Up to Be Cowboys"; and 1982 - "Just to Satisfy You")
Leon Russell (1979 "Heartbreak Hotel")
Merle Haggard (1983 - "Pancho and Lefty")
Julio Iglesias (1984 - "To All the Girls I've Loved Before")
Ray Charles (1984 - "Seven Spanish Angels")
Toby Keith (2002 - "Beer for My Horses")

As for related tandems, in over 60 years of Billboard and Cash Box pop charts there are only eight, and no doubt fewer than you thought:

Bellamy Brothers (David and Howard): "Let Your Love Flow" (1976)
Everly Brothers (Don and Phil): "Bye Bye Love" (1957); "Wake Up Little Susie" (1957); "All I Have to Do Is Dream" (1958); "Bird Dog" (1958); and "Cathy's Clown" (1960)
K-ci & JoJo (brothers Cedric and Joel Hailey): "All My Life" (1998)
Paul and Linda McCartney (married): "Uncle Albert/Admiral Halsey" (1971)
Nelson (twin brothers Gunnar and Matthew Nelson): "(I Can't Live Without Your) Love and Affection" (1990)
Nancy Sinatra and Frank Sinatra (daughter-father) "Something Stupid" (1967)
Sonny & Cher (married): "I Got You Babe" (1965)
Nino Tempo & April Stevens (brother-sister): "Deep Purple" (1963)

IZ ZAT SO? Here are some fun and fascinating facts regarding the rarity of related duos with No. 1 hits, based on 3,120 weekly charts, from 1940 through 1999:

Nino Tempo & April Stevens are the only brother and sister singing duo

Be they identical or fraternal, Rick Nelson's identical sons Gunnar and Matthew are the only set of twins

There are three sets of brothers (see above), but no sisters

Nancy and Frank Sinatra is our only father-daughter team, but neither mother-son nor mother-daughter acts are on the short list of pop chart toppers

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