Dancing With the Stars turned its ballroom into a live music showcase on Tuesday, Nov. 10, as Brandy and Monica, Sheryl Crow and Maren Morris performed during the competition’s first-ever “Grammy Night.”
The episode paired songs with Grammy history while six couples took part in side-by-side dance-offs, competing for the chance to remain on the show for another week. Each musical guest performed as two pairs presented simultaneous routines with their professional partners.
Brandy and Monica revisit “The Boy Is Mine”
Brandy and Monica reunited onstage for “The Boy Is Mine,” their 1998 collaboration that spent 13 weeks at No. 1 on the Billboard Hot 100.
The performance accompanied a rumba showdown between Amber Glenn and Ezra Frech. Glenn danced with pro Pasha Pashkov, while Frech was joined by Daniella Karagach.
“The Boy Is Mine” also fit directly into the night’s awards theme. The track won best R&B performance by a duo or group with vocal at the 1999 Grammys.
Crow brought a different sound to the ballroom with a performance of her 1994 song “All I Wanna Do.” Playing a glossy black guitar, she provided the soundtrack as Connor Wood and pro Rylee Arnold faced Maura Higgins and pro Mark Ballas in a cha-cha dance-off.
“All I Wanna Do” won record of the year and best female pop vocal at the 1994 Grammys.
Morris completed the lineup of live guest performances with “The Middle,” her 2018 collaboration with Zedd and Grey. Morris performed the song without her two recording partners as Jenna Dewan and pro Val Chmerkovskiy went head-to-head with Tatyana Ali and Jan Ravnik. Both couples also danced the cha-cha.
“The Middle” received Grammy nominations for record of the year and best pop duo/group performance in 2019.
Jenna Dewan receives a Janet Jackson message
Dewan and Chmerkovskiy won their dance-off against Ali and Ravnik, but the victory did not keep them in the competition. Dewan and Chmerkovskiy were ultimately eliminated at the end of the episode.
Earlier in the night, Dewan also performed to Janet Jackson’s “All for You,” which spent seven weeks at No. 1 on the Billboard Hot 100 in 2001.
Jackson, a five-time Grammy winner, made a cameo through a video message for Dewan.
“I am so excited,” Jackson said in the clip. “I cannot wait to watch you perform tonight.”
ShowBiz Take
The first “Grammy Night” gave Dancing With the Stars a way to connect its dance competition directly with live performances and awards history. Rather than appearing separately from the contest, Brandy and Monica, Crow and Morris became part of the dance-offs themselves, with their songs driving three simultaneous head-to-head matchups.
The episode also balanced celebration with the competition’s stakes. Dewan received Jackson’s personal message, performed to a seven-week Hot 100 chart-topper and prevailed in her dance-off, yet still became the week’s eliminated celebrity alongside Chmerkovskiy.
With Grammy-winning and Grammy-nominated songs at the center of the ballroom, the themed episode brought together live music, chart history and the pressure of elimination in one night.