In 1997, Maxwell was featured as a MTV Unplugged artist. On MTV Unplugged: Maxwell, he recorded songs from "Maxwell’s Urban Hang Suite" live, along with Nine Inch Nails hit, Closer and Kate Bush song, "This Woman’s Work". The album was produced by Alex Coletti. In 1998, Maxwell released his second album, "Embrya", which was a deeply spiritual album. "Embrya" had songs that reflected Maxwell’s search for self-understanding and self-enlightenment. Title tracks; "I’m You: You Are Me and We Are You", "Drowndeep: Hula", and "Submerge: Til we Become the Sun" reflect such views. "Embrya" serves to be a fan favorite especially with songs like "Matrimony: Maybe You", "Luxury: Cococure", and "Each hour each second each minute each day: Of My Life". Maxwell, Stuart Matthewman, and Darrell Smith served as producers for the album. Maxwell’s third album "NOW" which he produced was released in 2001 and debuted at the top of the Billboard charts. The album mostly was about the ups and downs people experience in life and learning from past mistakes. "NOW" has a wide variety of sounds from funk to soul to country, all sounds that blend well over the album’s R&B beats. On "NOW", Maxwell worked with long-time collaborators and friends, Hod David and Stuart Matthewman. From "Now", Maxwell released "Get to Know Ya", "Lifetime" and "This Woman’s Work" (remake of Kate Bush song).
In 1999, the hit single "Fortunate" was released and was featured on the soundtrack to the motion picture film "Life". The late 1990s film "Life", starred Martin Lawrence and Eddie Murphy. "Fortunate" written by R. Kelly, serves to be one of Maxwell’s biggest hits to date. Fortunate was awarded #1 Rhythm and Blues single of the year in 1999 by Billboard magazine. Also in the summer of 1999, Maxwell made a little girl’s wish to meet him come true. The little girl made her wish through the Make-A-Wish Foundation. A few months after meeting Maxwell the little girl died of cancer. Thus, prompting Maxwell to remake "This Woman’s Work" as a tribute to her.
Over the span of Maxwell’s career, he has been nominated various awards. Consecutively from 1996 to 2001, with the exception of 2000, Maxwell was been nominated six for Grammy Awards. Maxwell has also been nominated for a BET Award, Soul Train Music Awards, a NAACP Image Award, a MTV Video Music Award, and a Blockbuster Entertainment Award. Maxwell has won several Soul Train Music Awards, along with the award for number one R&B single of 1999, Billboard.