Taye Diggs is often considered one of Hollywood’s sexiest men.  However, before becoming an on-screen sensation, Diggs got his start on the stage. In 1996 he starred as rude landlord, Benny, in the production of the popular musical Rent, a role he later reprised for the film version in 2005.  Shortly after appearing in the stage production of Rent, Diggs made his transition to the screen.  The 43-year-old New Jersey native began moving toward mainstream success in the acting world after he made his first on-screen appearance in an episode of the now defunct crime drama, New York Undercover.  Throughout the 90s, Diggs also appeared in several films, and went on to land roles in some of the decade’s most memorable projects.  In the 2000s, Diggs’ career reached new heights, and he earned several award nominations including an Image Award nomination for Outstanding Actor in a Motion Picture.

Although Diggs has played a variety of characters over the years, he has become well-known for ability to play the sexy and sophisticated love interest.  According to Diggs’ he’s “I’ve always been attracted to women who are assertive and have confidence – qualities older women possess. They’ve been on the Earth a little longer. They’re more seasoned. They don’t play games. They know what they want, and they’re not afraid to tell you,” and those are exactly the kind of women he’s often attracted to on-screen.  Here are Taye Diggs’ five best on-screen romances.

5. Baggage Claim

In the 2013 film, Baggage Claim, Diggs played the role of Langston Jefferson Battle III, a womanizing opportunist who is running for Congress.  During the film, Diggs’ character, who is in search of a trophy wife, temporarily attempts to revive an old romance with main character, Montana Moore (Paula Patton). Although Baggage Claim received mostly negative reviews, one critic noted: “The best part of Baggage Claim, if such a thing is possible, is the section in which Montana quickly rekindles an old romance with Langston…” Although Diggs’ role in the film was minor, it was an interesting change of pace from his usual portrayal of kind and upstanding men.

4. The Wood

The 1999 film, The Wood, opens on Roland’s (Taye Diggs) wedding day.  However, Roland is nowhere to be found, and it quickly becomes apparent that he is experiencing some doubts.  Fortunately, Roland’s best friends from high school (Omar Epps and Richard T. Jones) are able to track him down at an old girlfriend’s house.  When the three meet up, they begin to reminisce on their younger years and Roland says that he misses his first love and high school girlfriend, Tanya (Tamala Jones).  Although a lot of the film takes place in flashbacks where the younger version of Roland isn’t played by Diggs, at the end of the film Roland and his friends return to the wedding, and he decides to marry his fiancé Lisa (LisaRaye McCoy).

3. Best Man

In the 1999 film, Best Man, Taye Diggs plays the role of Harper Stewart, a young author whose debut novel has been chosen by Oprah’s Book Club.  While Harper appreciates the honor, he is nervous for his close friends to read the book because he’s included many of their personal stories, including the fact that he’d slept with his college friend Jordan Armstrong (Nia Long).  Although Harper and Jordan were able to maintain a friendship after their physical encounter, it is clear that the two still have feelings for each other.  Unfortunately for Harper, his old feelings for Jordan seem to be holding him back in his current relationship with devoted girlfriend, Robin (Sanaa Lathan).  Although Harper’s relationship with Robin seems to be doing well, most fans can’t help but secretly root for Harper and Jordan to rekindle their old flame.

2. How Stella Got Her Groove Back

Based on the book of the same name, How Stella Got Her Groove Back marked Diggs’ first film role, and is the story of Stella (Angela Bassett), a middle-age stockbroker, who travels to Jamaica for vacation.  While on the island, Stella meets a young man named Winston Shakespeare (Taye Diggs).  Winston, who finds Stella attractive, begins to pursue her and the two form a romance.  Stella is enamored  by Winston and feels that he is the man of her dreams; however, the fact that he is half her age makes her feel uncomfortable about the situation.  Although the two have seem to develop real feelings for each other, Stella ultimately decides to return home at the end of the film, leaving many viewers to sympathize with Winston.

1. Brown Sugar

Popular for the line, “when did you first fall in love with hip-hop?” Brown Sugar has become a classic for hip-hop loving fans everywhere.  The film follows Dre (Taye Diggs) and Sidney (Sanaa Lathan), who have been friends since childhood.  Dre is an A&R for a fictional record company, while Sidney is the editor-in-chief of the popular hip-hop publication, XXL Magazine, and their love of hip-hop has always been a driving force in their relationship.  As the film unfolds, it is suggested that Dre and Sidney could be more than friends, although the two have never explored this possibility previously, and Dre and Sidney are both seeing other people.  After a conversation with her cousin (Queen Latifah), Sidney realizes that she has feelings for Dre and decides to tell him. Dre and Sidney eventually end up together, and in the year’s since the film’s release, they have become one of the most beloved on-screen couples.

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