As always, seniority first, which goes in favor of Brandy. She arrived on the scene in late 1994 with debut single “I Wanna Be Down” at just 15, which reached its No. 6 peak on the Billboard Hot 100 on New Year’s Eve. The single introduced her self-titled debut album, which spawned additional top 10s with second single “Baby” (No. 4) and fourth single “Brokenhearted” (No. 9).
Monica, meanwhile, was already on deck by the time Brandy hit the scene. Monica’s debut release, “Don’t Take It Personal (Just One of Dem Days)” debuted on the Hot 100 in April 1995 at No. 82, and two months later checked into its ultimate peak position of No. 2.
Despite the near miss, Monica’s debut set, Miss Thang, continued rolling out hits, with two more top 10s immediately following: “Before You Walk Out of My Life/Like This and Like That” (No. 7) and “Why I Love You So Much/Ain’t Nobody” (No. 9).
Both Brandy and Monica took a page from a common ‘90s strategy to sustain public interest between albums with appearances on soundtracks. Brandy took the Babyface-penned “Sittin’ Up In My Room” from Waiting to Exhale to No. 2, while Monica’s Space Jam single “For You I Will,” written by Diane Warren, climbed to No. 4.
Curiously, both had seen No. 2 singles, but it took their combined power to finally claim the Hot 100’s top rank. “The Boy Is Mine,” which played off an already-building media feud, exploded in the summer of 1998, leading the Hot 100 for 13 weeks and becoming the chart’s top-performing duet by two women in its entire history.
With “Boy” finally unlocking access to the summit, both Brandy and Monica returned to the Hot 100’s No. 1 rank again within the next year. Brandy led with “Have You Ever” in January 1999, while Monica reigned with both “The First Night” in October 1998 and “Angel of Mine” the next February.
Though those were their last Hot 100 leaders, the pair extended their chart victories in the R&B realm. Brandy has posted three top 5 hits on the Hot R&B/Hip-Hop Songs chart since 2000: “What About Us? (No. 3) and the Chris Brown-assisted “Put It Down” (No. 3).
Monica, meanwhile, has added four top five hits to her Hot R&B/Hip-Hop Songs count since the turn of the century. Two, “So Gone” and “Everything to Me” ruled the list for five and seven weeks, respectively, while “Love All Over Me” reached No. 2 and her guest turn on Keyshia Cole’s “Trust” helped it reach No. 5.
To sum it up, here’s a rundown of both Brandy and Monica’s biggest Hot 100 hits, with more than a few of these likely to show up during the showdown. And while “Boy” is the pinnacle of both artists’ careers, don’t count out a possible appearance from their overlooked second collaboration, 2012’s “It All Belongs to Me,” which reached No. 23 on Hot R&B/Hip-Hop Songs that April.
Brandy:
Rank, Song Title, Artist (if other than Brandy), Peak Position, Peak Date
1. “The Boy Is Mine,” with Monica, No. 1 (13 weeks), June 6, 1998
2. “Sittin’ Up In My Room,” No. 2, March 9, 1996
3. “Have You Ever?,” No. 1 (two weeks), Jan. 16, 1999
4. “I Wanna Be Down,” No. 6, Dec. 31, 1994
5. “Baby,” No. 4, March 11, 1995
6. “What About Us?,” No. 7, March 16, 2002
7. “Brokenhearted,” No. 9, Oct. 14, 1995
8. “Almost Doesn’t Count,” No. 16, June 19, 1999
9. “Full Moon,” No. 18, July 6, 2002
10. "Missing You," with Tamia, Gladys Knight & Chaka Khan, No. 25, Sept. 28, 1996
Monica:
Rank, Song Title, Artist (if other than Monica), Peak Position, Peak Date
1. “The Boy Is Mine,” with Brandy, No. 1 (13 weeks), June 6, 1998
2. “The First Night,” No. 1 (five weeks), Oct. 3, 1998
3. “Angel of Mine,” No. 1 (four weeks), Feb. 13, 1999
4. “Don’t Take It Personal (Just One of Dem Days),” No. 2, July 1, 1995
5. “For You I Will,” No. 4, April 19, 1997
6. “Before You Walk Out of My Life / Like This and Like That,” No. 7, Dec. 30, 1995
7. “Why I Love You So Much / Ain’t Nobody,” No. 9, July 6, 1996
8. “So Gone,” No. 10, July 12, 2003
9. “U Should’ve Known Better,” No. 19, July 31, 2004
10. “Everything to Me,” No. 44, April 10, 2010
