Jordan's first single was the 1995 No. 1 hit "
This Is How We Do It", which sampled
Slick Rick's earlier Def Jam hit "
Children's Story". The single reached No. 1 on the
Billboard Hot 100 and remained there for seven consecutive weeks. Thanks to the enormous success of the single, Jordan's first album went platinum, selling over a million copies. In 1996, Jordan opened for
Boyz II Men in
Vancouver. During the performance a stage flare disoriented him, causing him to fall off the seven-foot stage and hit his head. Despite being taken to the hospital, Jordan sustained no injuries. Jordan would later describe the event as a "modern-day miracle" and that he owed his life to Boyz II Men. Jordan followed up his success with "
Somethin' 4 da Honeyz", which peaked at No. 21. Later hits included "
Let's Ride" with
Master P and
Silkk the Shocker and "
I Like". He co-wrote, produced and sang back-up on
Shae Jones's 1999 album
Talk Show. The Jordan single "
Get It On Tonite" peaked at No. 4 in the same year. In addition to crafting his own material, Jordan has written and produced for other artists, including
Christina Milian,
98 Degrees,
Shae Jones,
Deborah Cox ("
Nobody's Supposed to Be Here", 1998),
Lil' Mo ("
Ta Da", 2000), and
Sisqó (the number-one hit "
Incomplete", 2000). The singer had a comedic supporting role in the film
The Fighting Temptations as Mr. Johnson, an aggressive convict who is self-conscious about his high-pitched voice. He made a cameo appearance in
The Nutty Professor, and he performed in the documentary
Standing in the Shadows of Motown. In 2000, his song "Unstoppable" was featured exclusively in the video game
NBA Live 2001. He performed the song "
Careless Whisper" together with musician
Dave Koz during the evening gown competition in
Miss Universe 2000, in Nicosia, Cyprus. In 2003 Jordan left Def Soul, citing artistic differences as the reason for the departure. In recent interviews, Jordan recalls issues he had with his image under Def Soul. In particular, Jordan wished to leave his image as a sex symbol behind and mature artistically. Jordan was marketed as a sex icon since his start at Def Soul, despite having been married to Kristin Hudson before even signing. Whenever he was asked about his relationship status, Jordan would simply respond that he was "married to [his] music." Realizing Def Soul was committed to maintaining Jordan's current image as their prominent R&B artist, Jordan left the label to sign with
Koch Records. That same year Jordan released the album
Life After Def under Koch. He contributed to the album of Croatian singer
Nina Badrić in the duet "Ne dam te nikom" ("I'm Not Giving You to Anyone"). Jordan's last release was 2008's
Let It Rain on the
Fontana Records label. Through 2015 and 2016, Jordan appeared at the halftime shows of various sporting games, as well as on
The Late Late Show with James Corden, performing "This Is How We Do It". In 2019, during an appearance on the SoulBack R&B Podcast, Jordan confirmed that he has recorded his first R&B album in over a decade and plans to release it this year. On May 19, 2019, Jordan sang "This Is How We Do It" on the finale of
American Idol, with a minor portion rapped by eliminated contestant Margie Mays, due to a performance of the song by Jake Puliti from earlier in the season in the audition round, which led to one of the memorable moments of the season with
Katy Perry doing
the worm. On November 19, 2019, Jordan was a guest on
Tamron Hall's talk show for her Throwback week series in which he performed "
This Is How We Do It". During the show, he talked about his upcoming album,
The Masterpiece, which would be released on November 29. In 2022, Jordan competed in
season eight of
The Masked Singer as "Panther". When Jordan was eliminated on "Vegas Night" alongside
Jeff Dunham as "Pi-Rat",
Nick Cannon stated to the panel that this is the one time that they didn't guess Montell Jordan like they did for the other contestants. In addition, Jordan also sang this show's rendition of "This Is How We Do It". ==Ministry career==