After releasing five albums with DJ Jazzy Jeff, Smith turned his focus to acting and appeared in such films as Bad Boys and Independence Day before returning to the studio in 1996.

[4] The songs on the album are broken up by a number of interludes featuring exchanges between Smith and the fictional character Keith B-Real, a "hilarious" magazine editor and motivational-tape artist.

[4] As with Smith's previous releases with DJ Jazzy Jeff, Big Willie Style showcases a radio-friendly pop-rap sound with non-explicit lyrics.

[1] Speaking about the lyrics on Big Willie Style, Jamie Hunter of Rolling Stone identified themes including multiculturalism and monogamy, commenting that Smith tells "the larger story of rap values tweaking the American dream, of how he's come to terms with the conflict between the neighborhood and the global cineplex".

[5][1] Artists sampled include Sister Sledge ("He's the Greatest Dancer" on "Gettin' Jiggy wit It"), Stevie Wonder ("Ribbon in the Sky" on "Chasing Forever") and The Whispers ("And the Beat Goes On" on "Miami").

Stephen Thomas Erlewine of website AllMusic awarded the album four out of five stars, praising Smith's "trademark ... friendly, humorous pop-rap" style, which he pointed out had been modernised since his releases with DJ Jazzy Jeff.

[5] Entertainment Weekly writer Jim Farber, however, slated the album, describing it as being full of "nonstop pop-rap clichés" and claiming that "The musical world suffered no great loss when Will Smith ditched rapping for acting".

[2] Village Voice critic Robert Christgau categorised the singles "Gettin' Jiggy wit It", "Just the Two of Us" and "Miami" as "good [songs] on an album that isn't worth your time or money".

[26] Big Willie Style earned Smith recognition at a number of music industry awards ceremonies.

[35] In 2000, music television network VH1 compiled their 100 Greatest Dance Songs list, including Smith's Big Willie Style single "Gettin' Jiggy wit It" at number 100.