Sliding across the living room in his underpants, juggling hard liquor and working his way back to the top after losing all of his sports clients, a young Tom Cruise starred in “Risky Business,” “Cocktail” and “Jerry Maguire.”

“Risky Business”

In this classic movie released in 1983, Cruise, at 21, plays Joel Goodsen when he films his most infamous scene dancing around in a pink button down and underwear while singing to Bob Seger’s “Old Time Rock and Roll.”

This film greatly appealed to a teenage audience, however, it also included lots of mature, adult-like aspects of life such as prostitution and alcohol. Despite his passion to attend college and make his parents proud, Goodsen allows his curiosity concerning the dangers outside his privileged life to distract him from his high school responsibilities. I was worried that he might blow his cover as a perfect child behaving responsibly while his parents were out of town. At one point, Goodsen can even be seen as an entrepreneur resembling a pimp.
I was on the edge of my seat every time Goodsen made another “risky” decision. I enjoyed watching Goodsen make rash and, quite frankly, unintelligent choices because it felt like I got to live through his character since I couldn’t ever dream of doing such things myself. Watching him accidentally let his father’s $40,000 Porsche roll into Lake Michigan made my heart drop and gave me the chills.

This wild ride, even through its cringeworthy moments and close calls, made the 1-hour-and-39-minute-watch entirely worth it. “Risky Business” perfectly encapsulates the secret teenage desire to break the rules and say, “What the heck.” It receives a four out of five star rating from me.

★★★★☆

“Cocktail”

In the 1988 movie, “Cocktail,” Cruise plays the role of Brian Flanagan, a young blue collar worker obsessed with making it big in the business world, but doesn’t have the education to back up his aspirations.

I found myself mystified by the many twists and turns in the relationship between Flanagan and his first boss, mentor and immediate best friend, Doug. I could never really settle on whether I liked or disliked his character until the end of the movie.

From the start, I supported Flanagan. I loved watching his character develop as the movie progressed, and he became more realistic with his goals. Cruise’s ability to exceptionally pull off two roles depicting entirely opposite characters absolutely blew me away. While Goodesen in “Risky Business” originates from wealth and aspires to go to college, Flanagan is dirt poor, avoids college and strives to succeed as an entrepreneur.

I would definitely rate this movie a four and a half out of five stars. “Cocktail,” a perfect blend of realism, romance and nightlife, is a great glimpse into the life of a struggling New Yorker through the perspective of a bartender with big dreams.

★★★★☆

“Jerry Maguire”

Cruise plays Jerry Maguire, a successful sports agent who goes through an internal conflict causing him to want to shift from simply collecting as many clients as he could, to focusing on fewer clients and building a stronger connection with them.

After a rough night of sleep, he creates a memo which he shares with the rest of his company that changes the future of his career for better or for worse. He finds himself unemployed and with only one of his sports clients, Rod Tidwell, which he clings to for dear life, as he reboots his career with the assistance of one employee who was willing to take the plunge with him. A phrase that makes numerous appearances throughout the movie is Tidwell’s infamous phrase: “show me the money!”

“Jerry Maguire” is a perfect balance between sports, business, love and comedy. I rate this movie a five out of five stars. Maguire goes from not being able to maintain a healthy romantic relationship to finding love where he least expected it, all because of an inner awakening that resulted in the creation of the memo. Similar to Flanagan in “Cocktail,” Maguire learns from his mentor and only long term client, Tidwell, that he needs to focus on each of his clients individually and build connections with them. However, before he can do that, he must, as Tidwell would say: “show me the money!”

★★★★★