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The Best Man: Then & Now

Now that The Best Man sequel, The Best Man Holiday, is coming out in November - 14 years after the original - we're taking a look back at the early work of the cast and writer/director, Malcolm D. Lee.

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    We love 1999's The Best Man! We're so excited that the original cast is reuniting 14 years later for a sequel, The Best Man Holiday. To get into the spirit for the upcoming sequel, we're taking a look at the cast as well as the writer/director Malcolm D. Lee - then and now!
    Photo: Ebony Magazine
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    Malcolm D. Lee is the writer and director of both The Best Man and its sequel. The Best Man was widely considered at the time of its release to be the male answer to the female-centric ensemble film Waiting to Exhale and is still one of the top ten highest grossing African American films in history.
    Photo: Getty Images
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    Malcolm D. Lee is the cousin of influential auteur Spike Lee. Spike lent a hand with The Best Man back in '99. 40 Acres and a Mule Filmworks, Spike Lee's studio, released the film with Spike himself serving as one of its producers. This is also the case with the upcoming sequel.
    Photo: Getty Images
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    Malcolm D. Lee's other film credits include Undercover Brother (2002), Roll Bounce (2005), Soul Men (2008), and Scary Movie 5 (2013). The Best Man was his debut directorial effort. He also made a cameo in the film as an emcee.
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    Taye Diggs plays the lead role of Harper Stewart in The Best Man series. Taye, short for "Scotty" or "Scottay", got his start in musical theater after attending Syracuse University. He was a dancer at Tokyo Disneyland and made his Broadway debut in the ensemble cast of the 1994 Tony Award winning revival of the musical "Carousel".
    Photo: Getty Images
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    In 1996 Taye originated the role of nasty landlord Benny in Jonathan Larson's Tony Award- and Pulitzer Prize-winning "Rent", alongside his future wife Idina Menzel. He also worked with her in other Broadway productions - "The Wild Party" and "Wicked".
    Photo: Getty Images
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    By the late 90s, Taye moved into television and film, starting with a role on "Guiding Light". Then he made a very memorable film breakthrough as Angela Bassett's very sexy, much younger love interest in How Stella Got Her Groove Back.
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    Next, in 1999, the same year as The Best Man, Taye Diggs starred in the coming of age drama The Wood. Diggs' future movie wife in The Best Man series, Sanaa Lathan, was one of his co-stars.
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    Morris Chestnut is Lance Sullivan, a professional football player on the eve of his wedding, in The Best Man. Chestnut has been in countless films since the early 90s but his acting debut was on television in a 1991 episode of "Freddy's Nightmares: A Nightmare on Elm Street: The Series".
    Photo: Getty Images
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    Following his television debut, his career really started to pick up steam. Morris Chestnut made an indelible impression as the tragically gunned down teenage father Ricky Baker in John Singleton's landmark drama Boyz in the Hood alongside Angela Bassett, Ice Cube, Cuba Gooding, Jr., Laurence Fishburne and future Best Man co-star Nia Long.
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    Following Boyz in the Hood, Morris Chestnut returned to TV in Patti Labelle's short-lived sitcom "Out All Night". After the show's cancellation, his career continued to rise steadily leading up to The Best Man with co-starring roles in big-budget films such as Under Siege 2 (1995) and G.I. Jane (1997).
    Photo: Jet Magazine
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    Sanaa Lathan is Robin, Taye Diggs' wife, in the Best Man series. Lathan's mother was a dancer who performed on Broadway with Eartha Kitt. Her father worked behind the scenes in television for PBS, as well as a producer on shows such as "Sanford & Son" and Russell Simmons' "Def Comedy Jam".
    Photo: Getty Images
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    A Yale Drama School graduate, Sanaa Lathan began her professional acting career with guest spots in several TV shows, such as "Family Matters" (she's shown here kissing Urkel!), "NYPD Blue", and "Moesha". Sanaa Lathan's next appearance was as Wesley Snipes' mother in Blade. She followed this with a role in Life with Martin Lawrence and Eddie Murphy and back-to-back turns in The Best Man and The Wood.
    Photo: YouTube
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    Lathan received a NAACP Image Award nomination for her performance in The Best Man. The Wood cast her as the love interest of her then-boyfriend Omar Epps. Lathan and Epps were reunited onscreen in her breakout film Love & Basketball, where she played a leading character instead of the girlfriend of one. Her performance earned her a NAACP Image Award as well as an Independent Spirit Award nomination and a BET Award. The nominations are still coming. Lathan later went on to be nominated for a Tony Award in a revival of "Raisin in the Sun".
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    Nia Long is Jordan Armstrong, Taye Diggs' close friend and former love interest, in The Best Man series. She's been a busy actress since childhood and is well known for her roles in "The Fresh Prince of Bel-Air", "Third Watch", "Everwood", "Boston Legal", Boyz n the Hood, Soul Food, Love Jones, Big Momma's House, Friday, and Are We There Yet?. In addition to acting, Long has directed some music videos - Yolanda Adams' "This Too Shall Pass" and Ashanti's "Baby".
    Photo: Getty Images
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    Nia Long started her career at a very young age, and her acting coach was Betty Bridges, better known as the mother of "Diff'rent Strokes" star Todd Bridges. One of her earliest roles was in the 1986 Disney television movie, The B.R.A.T Patrol. She actually made her TV debut the same year in a very small role on "227".
    Photo: YouTube
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    Her first notable role on television was a three-year stint as Kathryn "Kat" Speakes on the soap opera "Guiding Light". Long portrayed Kat from 1991 to 1994.
    Photo: YouTube
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    From 1994-1995, Nia Long played Will Smith's girlfriend and fiancée Beulah "Lisa" Wilkes on "The Fresh Prince of Bel-Air". Jada Pinkett-Smith was originally supposed to play Lisa, but was considered too short for the role (opposite a 6'2" Will Smith), thus leaving Nia to take the part.
    Photo: YouTube
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    Philadelphia-born Monica Calhoun is Mia Morgan, the bride who cheated on groom Morris Chestnut with the titular best man Taye Diggs in The Best Man. Like Nia Long, Calhoun is another child actress who managed to carve out a successful adult career. Her credits start in 1985 with the TV movie "Children of the Night". She appeared in several TV "Afterschool Specials" as well as a few sitcoms. Just out of her teens, she was nominated for an Emmy for her performance in the CBS Schoolbreak Special "Different Worlds: A Story of Interracial Love" in 1993.
    Photo: Getty Images
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    She continued to accumulate TV credits, including a 1993 guest spot on "A Different World" (shown here). Throughout her career, Monica Calhoun has worked with several members of The Best Man cast in other films and TV shows including "The Jacksons: An American Dream" (1992) as Rebbie Jackson opposite Terrence Howard's Jackie Jackson and as "Kerry" in Love and Basketball with Sanaa Lathan.
    Photo: YouTube
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    Academy Award and Golden Globe nominated actor/singer (and Philadelphia resident!) Terrence Howard plays The Best Man comic relief Quentin. Howard's original goal was to be a science teacher, but he left college after his acting auditions started landing him bit roles, such as a small guest spot on "The Cosby Show".
    Photo: Getty Images
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    Terrence Howard moved on to a somewhat larger but still supporting role in 1992 as Jackie Jackson in the TV miniseries "The Jacksons: An American Dream". He continued to accumulate minor credits in Who's The Man?, Dead Presidents and episodes of "Family Matters", "Living Single", "Coach", and "New York Undercover".
    Photo: YouTube
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    Terrence Howard, after struggling in bit roles for the first half of the 90s, made his big film break in 1995's Mr. Holland's Opus. He had graduated to more significant roles leading up to his supporting role in The Best Man. Howard wasn't really a major star until 2004/2005 when he broke even bigger with Crash, Hustle & Flow and Ray. By 2008, Howard was the highest paid actor in the first Iron Man. Yes, he had a bigger pay day than Robert Downey, Jr.
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    Regina Hall returns to the series as Candy, the kind-hearted stripper Harold Perrineau's Julian falls in love with in the first The Best Man. Outside of The Best Man, which was her first film, Hall is best known for her portrayal of Coretta Lipp in "Ally McBeal" for which she won a NAACP Image Award for Outstanding Supporting Actress in a Comedy Series.
    Photo: Getty Images
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    Regina Hall got her start in television commercials and with recurring roles on the soap opera "Loving" as well as "New York Undercover".
    Photo: Getty Images, YouTube
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    Regina Hall also appeared in the first four films in the Scary Movie series as Brenda Meeks. She also had a small role in Love & Basketball with fellow Best Man co-stars Sanaa Lathan and Monica Calhoun.
    Photo: YouTube
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    Melissa De Sousa returns as Shelby, the snobby ex-girlfriend of Harold Perrineau's Julian. Melissa's early career was heavily television-based. Her first role was in a "CBS Schoolbreak Special" in 1992. From there, she appeared on "Silk Stalkings", "Living Single", "The Sinbad Show", "Married with Children", and recreated the "Neely O'Hara" character in a short-lived 1994 TV reboot of the late 60s showbiz melodrama "Valley of the Dolls".
    Photo: Getty Images
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    Melissa also had a recurring role on early 2000s sitcom "One on One" as Natalie Odessa, Breanna's teacher who later dates Flex.
    Photo: YouTube
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    Harold Perrineau plays mild-mannered Julian Murch in The Best Man series. You may also remember him in recurring roles on "Oz" (as Augustus Hill), "Lost" (as Michael Dawson), and "Sons of Anarchy" (as Damon Pope). His career started in 1989 with a guest spot on "The Cosby Show" and on the stage. He originated the role of Tyrone Jackson in the world premiere of the stage adaptation of the 1980 hit movie Fame at the Walnut Street Theatre here in Philadelphia.
    Photo: Getty Images
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    Harold's first major film roles were in the independent dramedy Smoke (1995) with Harvey Keitel (a role for which he was nominated for an Independent Spirit Award) and very memorably in the 1996 Baz Luhrman adaptation of Romeo + Juliet as tragically loyal best friend (and sometime drag queen) Mercutio opposite Leonardo DiCaprio's Romeo.
    Photo: YouTube
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    Harold Perrineau also took on the role of Link, the pilot and operator for the crew of the Zion hovercraft Nebuchadnezzar, in the second and third films in the Matrix series.
    Photo: YouTube
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    Eddie Cibrian is joining the cast as Brian McDaniels in The Best Man Holiday.
    Photo: Getty Images
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    Among Cibrian's early roles is a stint from 1994-96 as Matt on "Young and the Restless". Other early appearances include spots on "Saved by the Bell: The College Years", "Beverly Hills 90210", "Sabrina the Teenage Witch", and breakthrough roles on "Sunset Beach" and "Third Watch".
    Photo: YouTube
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    Eddie Cibrian sang in the soul-pop boy band 3Deep from 1998 to 2001, along with "Young and The Restless" costar and real-life best friend Joshua Morrow and Canadian singer CJ Huyer.
    Photo: YouTube
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    Another early role for Eddie Cibrian was on the short-lived, very odd science-fiction inspired "Baywatch" spinoff "Baywatch Nights" alongside David Hasselhoff and Lou Rawls (who also sang the theme song). It was an attempt to merge the cheesy appeal of "Baywatch" with "The X-Files".
    Photo: YouTube