Last week I started talking about singers who tried and failed to have acting careers. Some failed right out of the gate while others were one-hit wonders. Now I’m going to finish where I left off and share the stories of singers who managed to hit the big time in Hollywood, as well as in the music industry.

If at First You Don’t Succeed

These singers refused to let their first few failures keep them from finding a surprising amount of success in the film world.

Madonna – Did you know Madonna’s acting debut wasn’t her supporting role in 1985’s Desperately Seeking Susan? It was actually 1979’s A Certain Sacrifice, a small independent film that barely even got a release date in the U.S. She then had a cameo in 1985’s Vision Quest, which is most notable for being produced by Jon Peters and Peter Guber a few years before they helped bring Tim Burton’s two Batman films to life.

After stumbling her way into Hollywood, Madonna had a surprisingly good role in the aforementioned Desperately Seeking Susan. She then wallowed in mediocre or worse films for the next few years, starting with 1986’s disastrous Shanghai Surprise, before enjoying a string of hits with 1990’s Dick Tracy, 1991’s Madonna: Truth or Dare, and 1992’s A League of Their Own.

The goodwill she built up with those hits went down the drain with her next group of films, starting with 1993’s Body of Evidence and ending with 1996’s Girl 6. That year, though, she starred in the titular role of Evita, which was a critical and box office hit. That was the last hurrah for the Material Girl, though. After a very uneven career full of hits and misses, it was all downhill from there. She had a cameo in the worst James Bond film ever, Die Another Day, and never starred in any film of note since then.

Vanessa Williams – Vanessa Williams started her film acting career inauspiciously with small roles in the 1987 Robert Downey, Jr. comedy The Pick-up Artist. The next year she graduated to costar of a brainless action film, Under the Gun, starring Sam J. Jones (of Flash Gordon fame). She then fell back to bit parts in her next two films, 1991’s Another You and Harley Davidson and the Marlboro Man. Nothing she had starred in up to that point had come close to earning a profit.

Williams took five years off and then returned as the costar in another brainless action film, Eraser. But this time it starred Arnold Schwarzenegger in the midst of his biggest blockbusters. The film wasn’t great, but it proved to be the vehicle she needed to get her acting career going. She followed that up with 1997’s successful Soul Food, but then had a bunch of not-so-spectacular films for the next few years. 2000’s Shaft remake was yet another action film that helped her career. She still acts and even sometimes stars in films, but it looks like she didn’t exactly save the best for last.

Justin Timberlake – Justin Timberlake’s first two films were released on the Disney Channel: 2000’s Longshot and Model Behavior. Neither was received terribly well. His next film, 2005’s Edison, was unmitigated disaster. 2006’s Alpha Dog and 2007’s Black Snake Moan got middling reviews, but then came Richard Kelly’s career-destroying film, Southland Tales. The film had a huge cast of big-name actors, but it failed on every level to be a good movie. Timberlake’s roles in the disappointing Shrek the Third and The Love Guru were also embarrassing. 2009’s The Open Road failed to earn even a measly $20,000 on its $10 million budget.

Everything seemed to be out of sync for Timberlake. His acting career was a disaster up to this point. But all that changed with 2010’s The Social Network. It was a critical and financial hit. He followed that up with the financially successful but critically panned Yogi Bear and Bad Teacher. Then came 2011’s Friends with Benefits and In Time, which both earned mostly positive reviews and healthy box office returns. His next few films (Trouble with the Curve, Runner Runner, and Inside Llewyn Davis) were received much more modestly. But this year’s animated Trolls looks to put Timberlake back on top and keep his acting career from going down the drain anytime soon.

Rihanna – 2012’s Battleship is an incredibly forgettable movie. If it goes down in history for anything, I submit it might just be remembered as Rihanna’s first film. The singer has taken several small steps into a promising acting career since that initial stumble. She had cameos in 2013’s This Is the End and 2014’s remake of Annie. Then she got a much more prominent role in the so-so but financially successful animated film Home. Next year she will appear in Luc Besson’s $200 million sci-fi film Valerian and the City of a Thousand Planets. Time will tell if that film will be successful and pave the way for Rihanna’s future success or if it torpedoes her budding career and proves to be the end.

Best of Both Worlds

Some actors, right from the start, managed to balance their acting and singing careers amazingly well, cementing their place in Hollywood history with multiple hit films.

Frank Sinatra – From Anchors Aweigh and From Here to Eternity to Ocean’s 11 and The Manchurian Candidate, Frank Sinatra has garnered more hits and awards than most other actors could ever dream of. Not bad for a man who is also one of the most popular singers of all time. There is more to say about Sinatra than I could even begin to do justice in this brief mention. I’ll just say that his films, which span nearly four decades, are well worth checking out.

Elvis Presley – Love him or hate him, Elvis Presley is the King of Rock and Roll Movies. From 1956 to 1969 he starred in 31 films! That is a breakneck speed for any actor, much less one who was also producing huge musical hits. The man could certainly entertain. While his films aren’t exactly all classics, and he didn’t get much of a chance to stretch himself dramatically as an actor, he did have more than a few hits, like Love Me Tender, Jailhouse Rock, Blue Hawaii, and King Creole, just to name a few. He was no Sinatra, but audiences couldn’t help falling in love with him.

Dolly Parton – Dolly Parton had an impressive acting career that spiked for about a decade before coming back to the Earth. Of all the actors on this list, she’s definitely the least prolific. She only had three movies that can be credited as solid hits: 1980’s 9 to 5, 1982’s The Best Little Whorehouse in Texas, and Steel Magnolias. She’s mostly just played herself in films and TV shows since then.

Bette Midler – Okay. Bette Midler is amazing. Take a gander at her filmography from 1986 to 1996: Down and Out in Beverly Hills, Ruthless People, Outrageous Fortune, Beaches, Disney’s Oliver & Company, Big Business, Stella, Woody Allen’s Scenes from a Mall, Hocus Pocus, and The First Wives Club. All substantial hits. Every movie she touched during that 10-year period was a success. Scenes from a Mall was the least successful of the bunch, and even that managed to triple its modest budget. From a distance, you might say she’s got quite a few wins beneath her wings.

No Acting Required

These films didn’t require the singers to play anyone but themselves. They mostly made autobiographical documentaries with a few exceptions.

The Beatles – The Beatles created a new subgenre when they made documentaries about themselves in the 1960s. They started with 1964’s A Hard Day’s Night and ended with 1970’s Let It Be. 1965’s Help! and 1968’s animated Yellow Submarine were exceptions to the usual formula, but the Beatles still played themselves in them. Rumor has it that they wanted to adapt The Lord of the Rings and The Three Musketeers into films starring themselves. But those projects never came to fruition, for better or worse.

Justin Bieber – The popularity of Justin Bieber arguably reached its apex in 2011 with the release of his concert biopic Justin Bieber: Never Say Never. It was a huge hit, grossing nearly $100 million. That makes it one of the highest-grossing concert films and documentaries of all time. Moviegoers avoided the 2013 sequel, Justin Bieber’s Believe, like the plague, and it went on to gross just $11 million. Maybe they should have called it Never Say Never Again.

One Direction – One Direction: This Is Us earned nearly seven times its $10 million budget in 2013. It’s one of the most popular concert films ever made. The musical group followed it up the next year with One Direction: Where We Are – The Concert Film. That managed to gross $15 million in a single weekend of release. Not bad. If things continue on that trajectory, this musical group might just be headed in the right direction.

A Category Unto Himself

One man defies categorization. He simply refused to play by any rules I tried to set down for him.

Michael Jackson – I’m bubbling with excitement to finish this article with the King of Pop. Michael Jackson is a category unto himself. Sure, he costarred with Diana Ross in 1978’s disappointing The Wiz. But he’s not exactly an “If at First You Don’t Succeed” kind of guy because that was the only theatrical film he starred in during his lifetime. He’s not a “Best of Both Worlds” kind of guy because he didn’t separate the two, but he combined movies and music in a way that no one else has ever come close to doing. And he’s not a “No Acting Required” kind of guy because he’s not just playing himself in his music videos; he’s playing distinct roles under the guidance of famed directors.

Take a look at this. Thriller was directed by horror/comedy director John Landis. Captain Eo was directed by Francis Ford Coppola. Bad was directed by Martin Scorsese! The “Smooth Criminal” part of Moonwalker was directed by Colin Chilvers, who won an Academy Award for his pioneering work on the special effects in Superman: The Movie. These are visionary filmmakers, and they all agreed to work on Jackson’s music videos in the midst of also working on acclaimed theatrical films.

Michael Jackson defied conventional thinking. He basically invented the music video and turned it into a respectable spectacle. He transcended Hollywood and the music industry to build something new that blended the two seamlessly. For that, he deserves to be left alone in his own category.

Giving It Their Best Shot

There are plenty of other singers who have made the jump from singing to acting, such as Ice Cube, Will.i.am, Tim McGraw, etc. My list of singers who try their hand at acting isn’t meant to be exhaustive but, rather, incisive. The first part of this article demonstrated it’s not easy to make the jump from one form of entertainment to another. Not everyone is a gifted actor, even if they have a voice to die for.

But that doesn’t mean there aren’t plenty of singers who have managed to bridge the gap and make something more of their careers by showing off their acting talent. I’m amazed by the people on this list. Even the ones who failed did so while giving it their best shot.

This is the Deja Reviewer bidding you farewell until we meet again.

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