21 Jesse McCartney
While it is safe to say that singer and former boy band member Jesse McCartney may have ultimately failed at monumental success in any category of fame and fortune, he hasn’t given up on his dream of acting stardom just yet. From snagging the lead on the beach drama Summerland to minor voice-over roles such as Theodore on Alvin and the Chipmunks, McCartney has seemingly ended his singing career and opted for one on the big screen—though whether or not he’ll be taken seriously is up to the industry.
22 Vanilla Ice
Though considered relatively irrelevant today, rapper Vanilla Ice has tried his hand at many talents—including acting. With a not-so-promising film debut in 1990’s Teenage Mutant Ninja Turtles II: The Secret of the Ooze (and plenty of other embarrassing projects, like Vanilla Ice Goes Amish and Da Hip Hop Witch), the rapper has become his worst enemy through a series strange and terrible tries at acting.
23 Jessica Simpson
The “With You” singer may not know what tuna is, but what she lacks in the kitchen has been made up for with her acting chops—or, well, she would like you to believe as much. Perhaps not entirely on purpose, Simpson has become the poster child for Hollywood’s affinity for casting pretty females into roles that require little acting. Case and point: her entire performance in The Dukes of Hazzard.
24 Usher
The award-winning R&B singer has managed to become one of the best-selling artists of all time; he’s sold 75 million records worldwide. And, as it turns out, throughout his time as an extremely successful musician, Usher was also digging into the film industry, making his debut as the lead character’s love interest on Moesha in 1997. Since then, he has appeared in minor roles in television and feature films alike, reminding us all that he still aims to be a triple threat—singer, actor, and heartthrob.
25 Queen Latifah
Though there is undoubtedly a larger percentage of the population who never knew Queen Latifah as the feminist rapper icon of the ’90s, the portion of the people who do remember her “Ladies First” days are mostly of the opinion that nothing she could do would ever change her image as rap icon. However, it seems as though the Queen of Hip Hop is attempting to rebrand herself as an actress, moving on to larger projects like Beauty Shop and Girls Trip with some critical acclaim, but not enough to overshadow her incredibly prolific career as a musician.
