Every Batman needs a Robin, right? Or every Kevin Spacey needs a Robin Wright. And like that, we’re off, talking about the best sidekicks on film. I’ll describe this as a target rich environment, full of great wingmen. Who has your back? Is it someone as loyal and cunning as Cosmo Brown? Can you trust them 100% of the time, in any situation?
Everyone needs a trusty sidekick. If you don’t have one, if you have the means, I highly recommend picking one up. They are so choice. When I talk about sidekicks, I am primarily talking about loyalty, enthusiasm, and friendship. I’m talking about someone who will follow you into battle, or if they are really cool, someone you can follow into battle. You don’t have to question them…ever. I want a sidekick. Here goes…
Best movie sidekicks
5) Randall Graves to Dante Hicks in Clerks (Kevin Smith, 1994). I almost had Silent Bob squeezing into my top five, but realized that most things I could write about Bob, I could also write about Randal. Randal and Dante have a connection that permeates their professional and personal lives. It’s love. It’s sweet…and crass. And Randal is not a great role model, but he has his buddy’s back. Sure he convinces Dante to close the store to attend the social event of the season, but when his old flame bounces back into his life, Randal let’s her know where she stands, warning, “Break his heart again this time, and I’ll kill ya. Nothing personal.” Not only that, but at the end when Dante and Randal basically destroy the Quick Stop, they help each other clean up. Who doesn’t need a friend like this?
4) Chewbacca to Han Solo in Star Wars (George Lucas, 1977). Every smuggler needs a seven foot Wookiie as a co-pilot. Serving a life debt to Solo, Han can always count on Chewie. Over the course of the original trilogy, Chewbacca allows Han to handcuff him in order to rescue Princess Leia, he helps Han and Luke in the destruction of the Death Star, he teams up to rescue his buddy from Jabba’s palace, and is instrumental in defeating the Empire on the moon of Endor. Not as much good conversation in this relationship, but Chewie would have to be a good listener, right? Plus he’s a mechanic, so he’s useful in other ways.
3) Doc Holliday to Wyatt Earp in Tombstone (George P. Cosmatos, 1993). Besides being handy with the steel, Doc is also an educated man, speaking Latin as eloquently as most people speak English. Doc is a good time. He’ll play cards with you all night, and not even call it a night if one of you starts coughing up blood. Even when stricken with severe symptoms from his Tuberculosis, he joins Wyatt in every gunfight, pretty much because he considers Wyatt to be his friend. Turkey Creek Johnson questions him, saying, “Hell, I have lots of friends.” Doc counters, “I don’t.”
2) Cal Naughton Jr to Ricky Bobby in Talladega Nights: The Ballad of Ricky Bobby (Adam McKay, 2006). Friends from way back, they both started working on pit row, and when they both made it as NASCAR drivers, still maintained that closeness. Cal was content to be Ricky’s number two, always swallowing his pride and putting the needs of his best friend first. He is also a supporter of Ricky’s entire family. If he was a dog, he’d be a golden retriever. Just watch the support he gives when Ricky Bobby is saying the blessing. Get you a friend that looks at you the way Cal looks at Ricky. Shake and Bake!
1) Goose to Maverick in Top Gun (Tony Scott, 1986). When I say sidekick, maybe I should say wingman. Goose calms Maverick as much as anyone can, he croons with him in public spaces, he basically saved his life by reaching a distant ejector handle, plus he accepts that Mav will occasionally cut a volleyball game short. And what a game – right ladies? He plays the piano, and accepts the good and bad of Pete Mitchell (see buzzing the tower). Basically Goose is that classic exemplar of fun and chill. You want him to show you the way home.
Get Your Shine Box 
I apologize for the length of this. I started to make my list, but the numbers got out of hand quickly. What I realized was that a good sidekick/wingman will have common characteristics and the good ones have several. I will explain those characteristics first, then assign them to my sidekick list individually.
1. Loyalty/Trust (LT) – The sidekick sticks by the hero no matter what. Most have this.
2. Team Player (TP) – The sidekick adopts the goals of the team as their own.
3. Sacrifice (S) – This is a step further than TP. The sidekick will compromise their own goals for the sake of the hero.
4. Hero Compliment (HC) – The sidekick is a strength where the hero has a weakness
5. Muse/Motivator (M) – The sidekick knows that the hero needs a pep talk from time to time to keep their focus on the goal.
6. Moral Compass (MC) – Similar to M or HC, but the sidekick needs the hero to not only stay focused on the goal, but not be willing to compromise principles in the process.
7. Yes Men (Y) – There’s a fine line between sacrificing your goals for the hero and becoming a Yes Man. Not a good attribute.
Ellis Boyd “Red” Redding, The Shawshank Redemption (1994) – LT, TP, S, M, MC – More of a close friend than a sidekick, but Red could be my favorite on this list.
Fezzik, The Princess Bride (1987) – LT, TP, S – The strength to compliment Inigo’s sword and Vizzini’s “brains”. Adapts to new allies and new enemies quickly. Ultimate team player.
Walter Sobchak, The Big Lebowski (1998) – LT, TP, M – Motivation personified. Keeps the Dude on task, otherwise they would just go bowling and forget about everything.
Napolean Dynamite, Napolean Dynamite (2004)- LT, S – Napolean is not the hero, Pedro is. Napolean is a glue guy that compliments both Pedro and Deb. Argument can be made he does the same for Uncle Rico and Kip.
Cledus “Snowman” Snow, Smokey and the Bandit (1977) – LT, TP, HC – Not sure he would be a good sidekick for anyone but the Bandit. Great complimentary sidekick.
Jack Burton, Big Trouble in Little China (1986)- TP, HC, M – The best part is that Jack thinks he’s the hero, but he truly is a sidekick…and a good one at that.
Sgt. Al Powell, Die Hard (1988)- TP, M – Devoted to the hero’s cause only a few minutes after “meeting” him.
Buzz Lightyear, Toy Story 2 (1999)- LT, S, HC – Woody helped Buzz, so now its time for Buzz to return the favor.
Dr Watson, Sherlock Holmes (any)- LT, HC, MC – The yin to Sherlock’s yang. The sum of these 2 is worth more than their separate parts.
Trent, Swingers (1996)- LT, TP, S, HC, M – Only missing the Moral Compass to be my complete sidekick. Trent sees the hero is down, so he takes it upon himself to lift him back up where he knows he can strive. Sacrificing his own rewards along the way.
Alfred, Batman (any) – LT, TP, S, M, MC – Alfred is the better Batman sidekick than Robin. Robin is just Batman Junior. Alfred gives Batman that pushback he needs plus the much needed MC.
Farmer Ted, Sixteen Candles (1984) – TP, S, M – Ted gives up on his quest for Samantha once he knew Jake was interested in her. Then completely buys in on Jake’s plans. Maybe too much of a pushover bordering on a Yes Man, but he was the bigger man by stepping aside.
Groot, Guardians of the Galaxy (2014)- LT, TP, S, HC – Lacks the vocabulary to provide much on the M/MC side. But he bought in on the larger team concept after already proving his loyalty to Rocket. He was willing to make a sacrifice for the new team.
Honorable Mentions:
Doc Brown, Back to the Future (1985)- LT, TP, HC, MC – The complete opposite of Marty, although one should question why they are friends in the first place.
Jack, Sideways (2004)- TP, HC, M – Along the lines of Walter from Big Lebowski, he keeps Miles on task to get what he wants. Granted, Jack does not compromise his goals, but making Miles happy is high on his list.
Garth Algar, Wayne’s World (1992)- LT, TP, S, Y – Maybe too much of a yes man, but its admirable that he sees Wayne’s victories as their victories.
Reed Rothchild, Boogie Nights (1997)- TP, Y – He was a sidekick because thats what the hero wanted. Recognizes the potential in Dirk and helps him along the way, but doubt that Reed ever had his own goals
Stiles, Teen Wolf (1985)- LT, TP, M – Motivates Scott to be bold and accept his wolfiness, instead of thinking of it has a negative.
Billy, Big (1988)- LT, TP, MC – Billy helps Josh remember who he is and where he came from. Probably not that much on the morals side, but he keeps Josh true to himself.
Brodie, Mallrats (1995)- LT, TP, S, M – Gives up his day to hang out with his friend, TS, to get him back on track. Willing to forego his goals to help TS.
Charles Del Mar, Better Off Dead (1985) – LT, M – Frames Lane’s outlook on being down and out as a test. Hypes up the man versus nature element by convincing Lane to ski the K12 to impress Beth.
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Wow. I think you may be the Bill James of this category. This easily could have been a top ten, right? I’m kicking myself about Trent from Swingers. When I first started making the list, Garth was in my list to. Excellent!
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