Whitney Houston vs. Heather Headley | Head 2 Head
![Whitney Houston vs. Heather Headley: Head 2 Head No. 9 (2025) [📷: Brent Faulkner / The Musical Hype; Arista, in:ciite; Israel Torres, KoolShooters, Los Muertos Crew, RDNE Stock project, Thomas Ronveaux from Pexels]](https://i0.wp.com/themusicalhype.com/wp-content/uploads/2025/04/whitney-houston-vs-heather-headley-head-2-head-9-2025.jpg?fit=768%2C768&ssl=1)
In the ninth edition of Head 2 Head (2025), Whitney Houston and Heather Headley contend for the best rendition of “All The Man That I Need.”
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Vicki Sue Robinson vs. Gloria Estefan | Head 2 Head
![Vicki Sue Robinson vs. Gloria Estefan: Head 2 Head No. 8 (2025) [📷: Brent Faulkner / The Musical Hype; RCA, Sony Music Entertainment, Inc.; Israel Torres, KoolShooters, Los Muertos Crew, RDNE Stock project, Thomas Ronveaux from Pexels; AcatXIo from Pixabay]](https://i0.wp.com/themusicalhype.com/wp-content/uploads/2025/03/vicki-sue-robinson-vs-gloria-estefan-head-2-head-8-2025.jpg?fit=768%2C768&ssl=1)
In the eighth edition of Head 2 Head (2025), Vicki Sue Robinson and Gloria Estefan contend for the best rendition of “Turn The Beat Around.”
Lauryn Hill vs. JP Cooper | Head 2 Head
![Lauryn Hill vs. JP Cooper: Head 2 Head No. 7 (2025) [📷: Brent Faulkner / The Musical Hype; Island, Ruffhouse, Universal Music Operations Limited; Israel Torres, KoolShooters, Los Muertos Crew, RDNE Stock project, Thomas Ronveaux from Pexels]](https://i0.wp.com/themusicalhype.com/wp-content/uploads/2025/03/lauryn-hill-vs-jp-cooper-head-2-head-7-2025.jpg?fit=768%2C768&ssl=1)
In the seventh edition of Head 2 Head (2025), Lauryn Hill and JP Cooper contend for the best rendition of “Ex-Factor.”
Five Stairsteps vs. Angie Stone | Head 2 Head
![Five Stairsteps vs. Angie Stone: Head 2 Head No. 6 (2025) [📷: Brent Faulkner / The Musical Hype; Sony Music Entertainment, Cleopatra; Israel Torres, KoolShooters, Los Muertos Crew, RDNE Stock project, Thomas Ronveaux from Pexels; AcatXIo from Pixabay]](https://i0.wp.com/themusicalhype.com/wp-content/uploads/2025/03/five-stairsteps-vs-angie-stone-head-2-head-6-2025.jpg?fit=768%2C768&ssl=1)
In the sixth edition of Head 2 Head (2025), Five Stairsteps and Angie Stone contend for the best rendition of “O-o-h Child.”
Tate McRae vs. ETHAN | Head 2 Head
![Tate McRae vs. ETHAN: Head 2 Head No. 5 (2025) [📷: Brent Faulkner / The Musical Hype; ETHAN, RCA; Israel Torres, KoolShooters, Los Muertos Crew, RDNE Stock project, Thomas Ronveaux from Pexels]](https://i0.wp.com/themusicalhype.com/wp-content/uploads/2025/02/tate-mcrae-vs-ethan-sports-car-head-2-head-5-2025.jpg?fit=768%2C768&ssl=1)
In the fifth edition of Head 2 Head (2025), Tate McRae and ETHAN contend for the best rendition of “Sports Car.”
Teddy Pendergrass vs. Kenny Lattimore & Chanté Moore | Head 2 Head
![Teddy Pendergrass vs. Kenny Lattimore & Chanté Moore: Head 2 Head No. 4 (2025) [📷: Brent Faulkner / The Musical Hype; Arista, Sony Music Entertainment; Israel Torres, KoolShooters, Los Muertos Crew, RDNE Stock project, Thomas Ronveaux from Pexels]](https://i0.wp.com/themusicalhype.com/wp-content/uploads/2025/02/teddy-pendergrass-vs-kenny-lattimore-chante-moore-head-2-head-4-2025.jpg?fit=768%2C768&ssl=1)
In the fourth edition of Head 2 Head (2025), Teddy Pendergrass and Kenny Lattimore x Chanté Moore contend for the best rendition of “Close The Door.”
The Spinners vs. R. Kelly | Head 2 Head
![The Spinners vs. R. Kelly: Head 2 Head No. 3 (2025) [📷: Brent Faulkner / The Musical Hype; Atlantic Recording Corporation, Zomba Recording LLC; Israel Torres, KoolShooters, Los Muertos Crew, RDNE Stock project, Thomas Ronveaux from Pexels]](https://i0.wp.com/themusicalhype.com/wp-content/uploads/2025/01/the-spinners-vs-r-kelly-head-2-head-3-2025.jpg?fit=768%2C768&ssl=1)
In the third edition of Head 2 Head (2025), The Spinners and R. Kelly contend for the best rendition of “Sadie.”
The Five Satins vs. Boyz II Men | Head 2 Head
![The Five Satins vs. Boyz II Men: Head 2 Head No. 2 (2025) [📷: Brent Faulkner / The Musical Hype; Ember, Motown, Universal Digital Enterprises; Israel Torres, KoolShooters, Los Muertos Crew, RDNE Stock project, Thomas Ronveaux from Pexels]](https://i0.wp.com/themusicalhype.com/wp-content/uploads/2025/01/the-five-satins-vs-boyz-ii-men-head-2-head-2-2025.jpg?fit=768%2C768&ssl=1)
In the second edition of Head 2 Head (2025), The Five Satins and Boyz II Men contend for the best rendition of “In The Still of the Night.”
Brandy & Monica vs. James Mac & Vall | Head 2 Head
![Brandy & Monica vs. James Mac & Vall: Head 2 Head No. 1 (2025) [📷: Brent Faulkner / The Musical Hype; Arista, Atlantic, Sweat It Out; Israel Torres, KoolShooters, Los Muertos Crew, RDNE Stock project, Thomas Ronveaux from Pexels]](https://i0.wp.com/themusicalhype.com/wp-content/uploads/2025/01/brandy-monica-vs-james-mac-vall-head-2-head-1-2025.jpg?fit=768%2C768&ssl=1)
In the first edition of Head 2 Head (2025), Brandy & Monica and James Mac & Vall contend for the best rendition of “The Boy Is Mine.”
Jennifer Holliday vs. Jennifer Hudson | Head 2 Head
![Jennifer Holliday vs. Jennifer Hudson: Head 2 Head No. 49 (2024) [📷: Brent Faulkner / The Musical Hype; Sony BMG Music Entertainment, Universal Music Enterprises; Los Muertos Crew, RDNE Stock project, Thomas Ronveaux from Pexels]](https://i0.wp.com/themusicalhype.com/wp-content/uploads/2024/11/jennifer-holliday-vs-jennifer-hudson-head-2-head-49-2024.jpg?fit=768%2C768&ssl=1)
In the 49th edition of Head 2 Head (2024), Jennifer Holliday and Jennifer Hudson contend for the best rendition of “And I Am Telling You I’m Not Going.”
Bobby Womack vs. K-Ci | Head 2 Head
![Bobby Womack vs. K-Ci: Head 2 Head No. 48 (2024) [📷: Brent Faulkner / The Musical Hype; ABKCO Music & Records, Inc., Geffen; Hernán Toro, Los Muertos Crew, RDNE Stock project, Thomas Ronveaux from Pexels]](https://i0.wp.com/themusicalhype.com/wp-content/uploads/2024/11/bobby-womack-vs-k-ci-head-2-head-48-2024.jpg?fit=768%2C768&ssl=1)
In the 48th edition of Head 2 Head (2024), Bobby Womack and K-Ci contend for the best rendition of “If You Think You’re Lonely Now.”
R.E.M. vs. Al Green | Head 2 Head
![R.E.M. vs. Al Green: Head 2 Head No. 47 (2024) [📷: Brent Faulkner / The Musical Hype; Athens L.L.C., Fat Possum, R.E.M.; Los Muertos Crew, RDNE Stock project, Thomas Ronveaux from Pexels]](https://i0.wp.com/themusicalhype.com/wp-content/uploads/2024/11/rem-vs-al-green-head-2-head-47-2024.jpg?fit=768%2C768&ssl=1)
In the 47th edition of Head 2 Head (2024), R.E.M. and Al Green contend for the best rendition of “Everybody Hurts.”