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Ask Billboard: What Are Your Favorite Madonna Songs?

Readers rank the Material Girl's best material. Plus, a trip through AC chart history and more songs that became hits three times.

As always, submit your questions about Billboard charts, as well as general music musings, to askbb@billboard.com. Please include your first and last name, as well as your city, state and country, if outside the U.S. Or, Tweet questions to Gary Trust: @gthot20


Hi Gary,

As you pointed out last week when ranking your top 20 Madonna tracks, everyone has different tastes. I checked my Madge playlists and found that having been with the Material Girl from the beginning makes no difference as to where her songs place.


From the moment I saw the video for “Human Nature” I was hooked. Perhaps not her best song for most people, but a powerful message that resonates strongly with me!

20, “Cherish”
19, “Like a Virgin”
18, “Open Your Heart”
17, “Like a Prayer”
16, “Beautiful Stranger”
15, “Material Girl”
14, “Secret”
13, “Deeper and Deeper”
12, “Frozen”
11, “Everybody”
10, “Vogue”
9, “Erotica”
8, “Music”
7, “Celebration” (Benny Benassi remix edit)
6, “Hung Up”
5, “Into the Groove”
4, “Sorry”
3, “Ray of Light”
2, “Express Yourself”

1, “Human Nature”

Stephen Scott
Brisbane, Australia


I couldn’t resist making a top 20 ranking of Madonna songs. I was a young tyke when she first came onto the scene, so I don’t really remember a world where Madonna wasn’t an icon.

20, “Love Don’t Live Here Anymore”
19, “Live to Tell”
18, “Devil Wouldn’t Recognize You”
17, “Who’s That Girl”
16, “He’s a Man”
15, “Gone”
14, “I Know It”
13, “The Power of Goodbye”
12, “Now I’m Following You”
11, “Sky Fits Heaven”
10, “I Deserve It”
9, “Human Nature”
8, “Amazing”
7, “Burning Up”
6, “Like a Prayer”
5, “Ray of Light”
4, “The Look of Love”
3, “Deeper and Deeper”
2, “Time Stood Still”

1, “Something to Remember”

Patrick Boothe
Austin, Texas


Hi Gary,

Madonna has so many good songs that a top 20 list can’t include them all. But, here’s mine:

20, “Material Girl”
19, “Burning Up”
18, “This Used to Be My Playground”
17, “Music”
16, “Dress You Up”
15, “Over and Over”
14, “What It Feels Like for a Girl”
13, “Open Your Heart”
12, “Gambler”
11, “Justify My Love”
10, “La Isla Bonita”
9, “Take a Bow”
8, “Hung Up”
7, “Into the Groove”
6, “Angel”
5, “Frozen”
4, “Crazy for You”
3, “You’ll See”
2, “Secret”

1, “Papa Don’t Preach”
Saludos cordiales,

Luis H. Sanchez Leyva

‘UP’ TO NO. 1

Well Gary,

I knew you’d never have another restful night’s sleep without my list of Madonna’s 20 best (like you, I also didn’t start to like her until a bit after she’d broken through, around her second album), so here goes:

20, “Stay”
19, “Justify My Love”
18, “Incredible”
17, “Candy Shop”
16, “Material Girl”
15, “Who’s That Girl”
14, “Till Death Do Us Part”
13, “Die Another Day”
12, “Oh Father”
11, “Erotica”
10, “Where’s the Party”
9, “Like A Virgin”
8, “Beautiful Stranger”
7, “Into the Groove”
6, “American Life”
5, “Music”
4, “Revolver”
3, “True Blue”
2, “Ray of Light”

1, “Dress You Up”

Need any more lists from me? Just holler!

David Fritz
Reseda, California


Hello Gary!

It was tough trying to rank my 20 favorite songs from one of my all-time favorite recording artists, but here’s what I came up with (in no particular order – I love ’em all, I can’t pick a No. 1!):

“Live to Tell”
“Into the Groove”
“Oh Father”
“Ray of Light”
“The Power of Goodbye”
“Bedtime Story”
“Hung Up”
“Don’t Tell Me”
“Causing a Commotion”
“Express Yourself” (non-stop express mix)
“Deeper and Deeper”

“4 Minutes” (feat. Justin Timberlake & Timbaland)
“I’ll Remember”
“Crazy for You”
“This Used to Be My Playground”
“Beat Goes On” (with Kanye West; should’ve been released as a single)

By the way, does anyone else notice that Madonna and the Billboard Hot 100 share birthdays only 12 days apart? The Hot 100 was born on Aug. 4, 1958 and Madonna on Aug. 16, 1958. It only seems right that she commands the lead for most top 10s (38) on the ranking!

Thanks Gary,

Ron Raymond, Jr.
Host/Producer, “Stuck in the 80s”
WMPG-FM and WMPG.org, Portland, Maine

Thanks all!

Not only do the Hot 100 and Madonna, the Queen of Pop, share the same birth month, so, too, does the King of Pop: the late Michael Jackson was born on Aug. 29, 1958. Jackson’s Hot 100 history includes 28 top 10s as a soloist, marking the most among men, a mark he shares with Stevie Wonder. (Among all acts, only Madonna and the Beatles (34) have more). Meanwhile, Jackson’s 13 solo No. 1s trail only the Beatles’ 20 and Mariah Carey’s 18.

Jackson additionally tallied 10 top 10s, including four No. 1s, with the Jackson 5.

As for Madonna’s next offering: her “MDNA World Tour” concert film arrives a week from today (Sept.10) on DVD, Blu-ray and as a digital album (via Live Nation and Interscope Records). The release runs two hours-long and sports songs from last year’s “MDNA” album and hits spanning her career. Check out the full track list here.

As always, submit your questions about Billboard charts, as well as general music musings, to askbb@billboard.com. Please include your first and last name, as well as your city, state and country, if outside the U.S. Or, Tweet questions to Gary Trust: @gthot20


@gthot20 Hey Gary, who holds the record for most #1 AC hits off a single album? I have Lionel Richie and Billy Joel with 4 from one album.

GMG @GrislyWing


With Phillip Phillips having become the ninth male artist to take his first two Adult Contemporary chart entries to No. 1 – “Home” and “Gone, Gone, Gone – perhaps it’s not too early to wonder if his debut album “The World From the Side of the Moon” might include more format toppers.

After both songs also crowned the adult alternative Triple A chart, third track “Where We Came From” is currently scaling the tally (28-25). With a clear hook, the midtempo track sounds like another potential AC hit.

As for who’s already banked the most AC No. 1s from an album? Here’s the list, starting with the select sets to generate four leaders apiece. Kudos for citing Joel and Richie. There was one more such album, however, which earned the honor in 1992:

Michael Bolton, “Time, Love & Tenderness” (1991-92)
“Love Is a Wonderful Thing,” “Time, Love & Tenderness,” “When a Man Loves a Woman,” “Missing You Now”

(A fifth single, “Steel Bars,” peaked at No. 7. Bolton wrote the song with Bob Dylan. Bolton reportedly recalls: “Someone who works with Dylan called me up and said, ‘Bob Dylan would like to write with you.’ I was awed. I told him, ‘I don’t even know how I could write a lyric when working with you – I’m too intimidated.’ But then we started messing around with some chords and wrote ‘Steel Bars,’ a song about obsession. It took us two sessions to write and when I left, I was told, ‘Bob likes you and he wants you to come back.’ “)

Lionel Richie, “Can’t Slow Down” (1983-84)
“All Night Long (All Night),” “Hello,” “Stuck on You,” “Penny Lover”

(Second single “Running With the Night” reached No. 6.)

Billy Joel, “An Innocent Man”  (1983-84)
“Tell Her About It,” “An Innocent Man,” “The Longest Time,” “Leave a Tender Moment Alone”

(The set also produced the No. 2-peaking “Uptown Girl” and No. 3 “Keeping the Faith.”)

Meanwhile, 14 other albums have yielded an also impressive three AC No. 1s each:

Adele, “21” (2011-12)
“Rolling in the Deep,” “Someone Like You,” “Set Fire to the Rain”

Kimberley Locke, “Christmas” (2005-07)
“Up on the Housetop,” “Jingle Bells,” “Frosty the Snowman”

Celine Dion, “Falling Into You” (1996-97)
“Because You Loved Me,” “It’s All Coming Back to Me Now,” “All By Myself”

Mariah Carey, “Mariah Carey” (1990-91)
“Vision of Love,” “Love Takes Time,” “I Don’t Wanna Cry”

Wilson Phillips, “Wilson Phillips” (1990-91)
“Hold On,” “Release Me,” “You’re in Love”

Gloria Estefan & Miami Sound Machine, “Let It Loose” (1988)
“Can’t Stay Away From You,” “Anything for You,” “1-2-3”

Whitney Houston, “Whitney” (1987-88)
“I Wanna Dance With Somebody (Who Loves Me),” “Didn’t We Almost Have It All,” “Where Do Broken Hearts Go”

Whitney Houston, “Whitney Houston” (1985-86)
“Saving All My Love for You,” “How Will I Know,” “Greatest Love of All”

Kenny Rogers, “Share Your Love” (1981-82)
“I Don’t Need You,” “Share Your Love With Me,” “Through the Years”

Barry Manilow, “This One’s for You” (1976-77)
“This One’s for You,” “Weekend in New England,” “Looks Like We Made It”

Captain & Tennille, “Song of Joy” (1976)
“Lonely Night (Angel Face),” “Shop Around,” “Muskrat Love”

John Denver, “Windsong” (1975-76)
“I’m Sorry,” “Fly Away,” “Looking for Space”

Carpenters, “Horizon” (1975)
“Please Mr. Postman,” “Only Yesterday,” “Solitaire”

Carpenters, “Carpenters” (1971)
“For All We Know,” “Rainy Days and Mondays,” “Superstar”

(And that’s how you turn 140 characters into an essay covering 42 years of history dating back to the Carpenters.)

As always, submit your questions about Billboard charts, as well as general music musings, to askbb@billboard.com. Please include your first and last name, as well as your city, state and country, if outside the U.S. Or, Tweet questions to Gary Trust: @gthot20


Hi Gary,

Here’s one song that wasn’t mentioned in your list in the last “Ask Billboard” about songs that have charted three times: “I Honestly Love You” by Olivia Newton-John.

Its Hot 100 peaks:
No. 1 (two weeks), 1974
No. 48, 1977
No. 67, 1998


Jim Sargent
Minneapolis, Minnesota


On your topic of three-time hits, Prince’s “1999” hit No. 44 on the Hot 100 in its initial release in 1982, No. 12 in its re-release (following “Little Red Corvette”) in 1983 and No. 40 when it re-charted for a week in 1999.


Chris Feldman
Dubuque, Iowa

Thanks Jim and Chris for … second-guessing … the idea that the list in last week’s mailbag was complete.

And, one more that kind of fits (to add a third such song …): Bruce Hornsby’s “The Way It Is,” especially since he just landed his second No. 1 on Billboard’s Bluegrass Albums chart with Ricky Skaggs, “Cluck Ol’ Hen: Live.” (They teamed up for the 15-week leader “Ricky Skaggs & Bruce Hornsby” in 2007.)

The song originally topped the Hot 100 as the title cut from his first set, with his backing band the Range, in 1986; Hornsby released a live version on his 2000 album “Here Come the Noise Makers”; and his new set with Skaggs offers a bluegrass reinvention of the song.

Meanwhile, in 1999, 2Pac’s song “Changes,” which samples “The Way It Is,” added to the reach of Hornsby’s equal rights anthem. “Changes” reached No. 32 on the Hot 100, No. 12 on Hot R&B/Hip-Hop Songs and No. 2 on Rap Songs.