How many songs had made to top 40 at least twice, in versions by male and female performer(s)

I had trouble wording the title, but the question was posed by thinking about how “You Keep Me Hanging On” charted first by the (female) Supremes and later by the (male) Vanilla Fudge.

Any other songs appear on the charts sung first by one gender and later by the other?

“Loco-Motion,” Little Eva, Grand Funk Railroad, Kylie Minogue

“Crimson and Clover,” Tommy James, Joan Jett

“I Will Survive” First by Gloria Gaynor and then somewhat recently by Cake.

Well, if you count the Dutch charts, “If Not For You” reached 30 by Bob Dylan, and 11 by Olivia Newton-John. Surprisingly, George Harrison’s version never charted anywhere in the world that I can find - probably because I don’t think it was ever released as a single.

I am not sure how it played, but “You Don’t Bring Me Flowers” was released more or less simultaneously by Neil Diamond and Barbra Streisand. I recall hearing a DJ’s cut of the two solo works into a faux duet. In modern parlance, it went so viral they went back to the studio and recorded it that way. I am pretty sure the duet was high on the charts, and so was Diamond’s… not sure about Barb’s. I don’t know of many cases quite like that one.

American Pie, though most people insist there was only one version.

“I Think We’re Alone Now.” Tommy James and the Shondells and Tiffany. Both made it to #1, which may be the only example of that you’ll find using this thread’s parameters.

“A Hazy Shade of Winter,” Simon & Garfunkel, The Bangles
“MacArthur Park,” Richard Harris, Donna Summer
“Respect,” Otis Redding, Aretha Franklin

I already mentioned “The Loco-Motion.” Both the Little Eva and Grand Funk versions made #1.

“I Heard It Through the Grapevine” - Both Marvin Gaye and Gladys Knight charted with it (#1 and #2 respectively.)

“Proud Mary” - First by Creedence Clearwater Revival and later by Ike & Tina Turner

“You Can’t Hurry Love” The Supremes and Phil Collins

What female cover made the top 40?

Madonna’s reached #29 in the US. (Despite not being released as a single…)

Madonna

D’oh Ninja’d

Can’t neglect cover queen Linda Ronstadt:

When Will I Be Loved (Everly Brothers)

That’ll Be the Day (Crickets)

Blue Bayou (Roy Orbison)

If you expand the criteria to the UK charts, there’s also::

I Can’t Let Go (The Hollies – missed the US Top 40 by a bit, but was Top 10 in the UK)

You’re No Good (The Swingin’ Blue Jeans’ cover made the UK charts)

I’m away so can’t consult my chart books for verification. There’s also “it’s So Easy,” but I don’t think Buddy Holly’s version charted.

Abraham Martin & John: Dion, Miracles, Moms Mabley
Ain’t That A Shame: Pat Boone, Fats Domino, 4 Seasons
Ain’t Too Proud To Beg: Temptations, Rolling Stones
Alfie: Cher, Dionne Warwick
All By Myself: Eric Carmen, Celine Dion
All Cried Out: Lisa Lisa & Cult Jam, Allure
Along Came Jones: Ray Stevens, Coasters
Always And Forever: Heatwave, Whistle

“Landslide” written by Stevie Nicks, performed by Fleetwood Mac, Smashing Pumpkins, and Dixie Chicks.

The original only made it to #4. ETA: In the US. There is also the Girls Aloud version which made the UK top five.

I think you might have missed the part about “male and female performer(s)”.

“Ain’t to proud to beg” works anyway: TLC