Top 10 Sylvester Stallone Movies of the 80s and 90s

How can you not love Over the Top? I thought this was the perfect way to start my top 10 Sylvester Stallone movies of the 80s and 90s list. I have fond memories of watching this when I was a kid and to this day as a 40-something, if I am wearing a cap, I will do the whole turn it around thing just like Lincoln Hawk does.

In this movie, Lincoln is a truck driver who wants to build a relationship with his estranged son, start his own trucking company, and also win the big arm wrestling championship. It is easy to poke fun at Over the Top for being a movie about arm wrestling, but great performances and the great work of director Menahem Golan make this a fun and heartwarming movie that always makes me smile.

Cobra is a gritty 80s action movie and I feel it’s become more appreciated over the years! In this movie, Sylvester Stallone plays the role of a badass cop called “Cobra” and he is part of the Zombie Squad that is there to clean up the streets. He ends up in this hostage situation that puts him on an even more dangerous path.

He is not only cleaning up the streets of crime, but he also has a key witness that he needs to protect as well. This is about as 80s as you can get when it comes to Stallone and I love this movie for that! A couple of fun bits of trivia with this movie: once again Stallone teamed up with his then-wife, Bridgett Nielson, and there was also a computer game based on this movie released for a few different home computers.

Look, I am not proud of this, but 1993’s Cliffhanger was a movie that I saw on a pirate VHS that I borrowed from a friend at school back in the day! I had to have Cliffhanger on this top 10 Sylvester Stallone movies of the 80s and 90s list. Here, Stallone plays the role of a rescue ranger called Gabe who ends up in a pretty tragic situation that sees him wanting to walk away from this line of work.

Well, he doesn’t get to walk away as some cash is missing in the Rocky Mountains and so are some people. He finds himself in a very dangerous situation with some desperate and crazy characters looking for that money! While this is a Stallone list, I do have to say that the absolute highlight of Cliffhanger is the insane and over-the-top performance by John Lithgow as the villain! Also, I want to give props to the fun video game tie-in for the Sega CD which was a technical marvel when it was released.

We are going back to the 80s with 1989’s Tango & Cash! What is there not to love about Tango & Cash? Here we have Stallone teaming up with Kurt Russell and they are such a great pair. These guys are two cops that have very different styles and personalities. One works the Eastside of L.A. and the other the West, but they are forced to work together to try and clear their names.

This is a fantastic action comedy with some awesome moments. This is the kind of movie that is perfect to put on if you’re in the mood for some classic 80s action and style. With all the big remakes and reboots that Hollywood loves to do, I am surprised that they have never thought about getting Stallone and Rusell back together to play Tango & Cash once again!

I remember a big deal being made about how much weight Stallone had to put on for his role as Sherrif Freddy Heflin in Cop Land. In this movie, Stallone really gets to let his acting chops show. He does a great job too, as this film features an amazing cast with Harvey Keitel, Ray Liotta, Robert DeNiro, and many more great actors. Stallone more than holds his own here.

This is a great movie in which Sheriff Heflin ends up in real trouble with some corrupt cops and the mob, who use his little town as their own personal playground. I had to feature this on here as it is not just one of the top 10 Sylvester Stallone movies of the 80s and 90s, it is a fantastic movie in its own right. If you love cop/mob/crime dramas and have never seen this, I highly recommend you watch it. I’ll be sure not to spoil it, as it has some great twists and turns! 

Next up we have a real personal favorite of mine, and that is 1995’s Assassins. What we have here is a very entertaining action thriller that sees Sylvester Stallone go head to head with Antonio Banderas. Stallone plays the role of an elite hitman called Robert Rath. Robert wants to retire, but he is given one last job that will allow him to do so.

Things get complicated when a younger hitman, Miguel Bain, comes into his life. Antonio Banderas as Miguel Bain is amazing! He loves Rath and wants to replace him as the top hitman in the world.

During Rath’s last job, things get very complicated and he ends up trying to protect his target and stay one step ahead of Bain, all the while trying to figure out what is going on. I love this movie and even though I know what is going to happen, I am always entertained when I watch this! The chemistry between Stallone and Banderas is amazing, especially the scene with the two of them in the car.

We are staying in the 90s on our top 10 Sylvester Stallone movies of the 80s and 90s list as we talk about Demolition Man! Released in 1993, Demolition Man is a whole lot of fun. Stallone plays the role of an elite LA cop called John Spartan who is sent to deal with a hostage situation where acclaimed bad guy, Simon Phoenix, is causing trouble.

Things do not go as planned and as a punishment, John and Simon are cryogenically frozen. Fast forward to the distant future of 2032 and Simon manages to escape and he goes on a rampage in this “futuristic” LA. They decide to thaw out John Spartan – as this modern nonviolent society is not equipped to deal with a madman like Simon Phoenix!

From the stuff with the “three seashells” to the VR sex to eating rats, Demolition Man is one of those movies that has a ton of memorable scenes. Of course, we are talking about our main man Sly here, but we also have to talk about how great Wesley Snipes and Sandra Bullock are in this movie too. As I write this, 2032 is less than 10 years away, and I can pretty confidently say that 2032 is not going to look like it does in Demolition Man!

If it were not for Rocky and Rambo, Lock Up would be my favorite Stallone movie of all time! I got my first VHS player in 1991 for Christmas and Lock Up was one of the first movies I got with it. What we have here is a thrilling movie where Sylvester Stallone plays the role of a prison inmate called Frank Leone. Frank is a model prisoner and is incarcerated at a minimum security prison. He is just about ready to be released.

One night, guards come into his cell and take him to a brutal maximum security prison headed by a corrupt and evil warden played by Donald Sutherland. He and Leone have a complicated past and he wants to make Leone suffer.

We see Leone get abused by the guards and the prisoners and it can be hard to watch. Leone is a really good guy and it is impossible not to feel for him. There is a football game in this movie that is up there with the best football games in cinematic history! I think that Frank Leone outside of Rocky and Rambo is Stallone’s most likable role and Lock Up is a movie that I feel deserves way more love than it gets.

Let’s face it: when you started reading this top 10 Sylvester Stallone movies of the 80s and 90s, you knew that a Rambo movie would make it into the top 3! I loved Rambo growing up! My dad was a huge fan and we would watch these movies all of the time. To be honest with you, the first three are all interchangeable for me, but I think I slightly prefer First Blood to the other two. In this movie, Stallone plays the iconic role of John Rambo.

Rambo is a troubled Vietnam War veteran and he ends up in a small town that is run by a corrupt sheriff. Brian Dennehy as Sherriff Will Teasel is so awesome, he is well and truly a bad guy that you love to hate.

We have a ton of people that are out for Rambo’s blood, but he is the ultimate survivor and he uses all his skills to not just survive, but take down these people that look to do him harm. I love Rambo and even the 2008 Rambo movie I thought was great. The less said about Rambo: Last Blood the better though!

Rocky to me is one of the greatest film franchises of all time, and I like all six of the Rocky movies and all three of the Creed movies. When I knew I was only putting one Rocky movie on this list, there was no hesitation, I knew it was going to be Rocky IV!

At the time I saw this, the death of Apollo Creed (along with Optimus Prime in the Transformers movie) was the most shocking thing that I had seen in a movie! I loved Apollo Creed and I wanted nothing more than for Rocky to get his revenge on that big evil Russian, Ivan Drago! Some may argue that Rocky IV is nothing more than a training montage, but I do not care. This well and truly always gets my “heart on fire” and it is just so much fun.

That end fight is brutal and in typical Rocky fashion, we get to see him grow as a person. I also love how we see Drago doing the latest training along with the latest “supplements” while Rocky is training like a badass in the snow and mountains. While I love all the Rocky movies, nothing hit me harder than Drago killing Apollo!