It’s been almost 30 years since we last saw Happy Gilmore, the former hockey player who won the Tour Championship in 1996. Since then, life has vastly changed. He married Virginia (Julie Bowen), the pro-golf-tour PR director from the first film, and had four sons and one daughter with her. His golfing success continued to grow, with him winning six championships. Nothing could stop Happy’s win streak but a cruel twist in fate. During an event, one of his tee shots kills Virginia, striking her in the head in a freak accident. Happy suddenly found himself a widower with five children. The pain of her death resulted in Happy swearing off golf and replacing his sorrows with alcohol.
Now 58, Happy is a mess. He works in a supermarket, constantly drinking from various flasks throughout the day, including during family time. He’s sad and depressed, just going through life’s motions. Despite his grief, he refuses to disappoint his daughter, Vienna. She has been accepted into the Paris Opera Ballet School, and even if it costs 75,000 a year to attend, Happy is determined for his daughter to attend. But the only way to accrue that much money quickly is to enter into golf tournaments and clean up his life, starting with getting sober (technically because he was court-mandated). There, he finds Ben Stiller’s sadistic retirement-home aide Hal—now a 12-step abusive guru who leads the recovery program.

Despite the chaos Hal brings to Happy and others in the group, he meets Bessie, a hilarious fellow alcoholic who supports him and his career, played by the legendary Kym Whitley. In celebration of Netflix’s Happy Gilmore 2, The Koalition spoke to her to learn more about her approach to Bessie, learning on the fly, improv acting, the importance of costumes, and more.
Dana Abercrombie: Can you talk about your approach to comedy and how each role informs both the comedic timing and personality? How do you find the approach to characters and their humor?
Kym Whitley: It’s really about who you’re in the scene with. This is very important because if you’re in the scene with other people who don’t have comedy timing, it’s difficult. It’s like playing volleyball; you’re back-and-forth, back-and-forth. Sometimes people have to play the straight person, but that does not mean they’re not funny. Their straight person has to be good at timing, also. The approach is really to know your lines, know where you’re coming from, and not be so married to the lines. That’s really important because you’re doing an Adam Sandler film. He’ll let you improvise, so you really want to come with your loaded gun of comedy and be ready.
With the character of Bessie, there was not a lot of preparation compared to a drama. I actually had her totally opposite. Once I got on the set, they were like, ‘No, Kim, we’re going to do it this way.’ I was like, ‘What? It’s really just trusting the director [Kyle Newacheck]. Kyle was really good at that, and Adam let us find our way.”
Dana: Can you talk about finding that opening of what you thought the character was and how it was different than what they wanted? What was the nature of the pivot? Was it on the fly, or did you have room to figure it out?
Kym: A little bit on the fly. Adam will throw stuff at you and Kyle. They’ll say, ‘try this.’ And they’re laughing and having fun. I’m like: ‘This is not funny. Y’all want me to hurry up and change? Oh, y’all think it’s funny.’ And they do because they’re like: ‘Oh, Kim, you can do it. Go ahead.‘ They trust you as a stand-up comic and an actress to be able to make a pivot. And that is really nice because you’re on a set where you’re comfortable and they trust you and you trust them.
We have a scene where we’re running down a hill. And during the running scene, I was like, “cut, cut, cut.” I was like: “Listen, I’m not; I can’t do all this.” I said, “I’m running downhill. I got heels on. My chest is bouncing.” And they thought it was funny. I was like, “Can I half-run, and can I stop and do some funny things?” They were like, “Yeah, try it. Try it.”
Then we did one side and then the other. And then I swear they just grabbed a neighbor’s dog. I’m telling you, some random dog. I was like a scene a minute ago. They’re like, ‘We’re going to just try it.’ I was like, “Y’all just took the neighbor’s dog?” So, it made it just a lot of fun. I looked at her. I knew she was going to become friends with Adam and where she was.”
With the characters I play, I try to do my research. I’ll go on YouTube and look at people who are in that situation and how they act, because when it’s a comedy, it is not that deep. I picked up a couple of characteristics, and when I got on the set, they were like, “Ah, we changed it. We’re going to do something else.“
What? She’s not that? What? What? They were like, “You know, Kim, just be you.” So in a comedy—unless you’re doing a character who has certain characteristics—it’s not difficult. Every character has a part of me, so it doesn’t make it as deep. Even when I did You People with Eddie Murphy, they were like, “Kim, come do this part. What? You’re going to be one of the wedding people.” I was like, “Where are the lines?” They’re like, “Kim, just say whatever.” What? That’s it. It’s always fun when you work with producers and directors who know you. They’re like, “Do your ‘Kim-ism.” So, it makes it fun. When I’m developing the character, I just have to be funny, so I do a lot of improv work on stage. It helps in my training.

Dana: In your career, does the acting fuel the comedy, or is it the other way around?
Kym: The comedy fuels the acting, and they go hand in hand. But when you’re on stage with a live audience, coming through that whole era of just working on it all the time, you are performing. That’s what acting is. You’re performing, and in certain stand-ups, you act it out. That’s part of the formula for stand-up. You have the setup, then you have the act-out, then you have the retort to bring it back around. In your act-out, you’re performing. If I’m talking about my dad, I’m acting out my dad, or I’m acting out my mom or my brothers, or my girlfriend. I really feel like stand-up fuels the acting and vice versa.
Dana: Can you talk about the importance of costumes? Do you base a character around what the wardrobe would look like, or is it how the wardrobe highlights the established personality?
Kym: Wardrobe is really important. People don’t understand that wardrobe goes hand in hand with their character. When you’re a young actor, you don’t understand that because you let them put you in anything, and you don’t feel the character. When I did Curb Your Enthusiasm, they knew good and well I was going to be a prostitute. Baby, they put me in some horrible prostitute roles, which were good but horrible. I was like, “Oh, like I’m a real prostitute.” But it went with the character. If I had been fully dressed, it would have made sense. And that’s what people have to understand.
With Happy Gilmore 2, they had choices, and they always say, “Do you like this? Do you feel comfortable in this?” What? I was like, “Oh, yeah. Well, let’s, you know, maybe we should do this. Let’s throw a head wrap on. Let’s do this and that.”
It’s always important to be in the conversation with the customer about your character.
Dana: When surrounded by comedians in a movie like Happy Gilmore 2 or on stage, is the cast trying to one-up each other, or is everyone bouncing jokes and ideas back-and-forth?
Kym: A lot of times, especially with male comics, you get in a room with them and they’re all trying to one-up each other. You don’t see female comics doing that. We just don’t do that. We’re going to be funny in our own right, but we don’t try to one-up each other. Male comics do. I believe in a film, people try to one-up, but what you find is that the people who try to really one-up are hungrier than you. They are. They have not shined in this industry yet. So, they’re really overpowering you. The best duel is when one comic leaves room for the other comic to shine and vice versa, and you both shine. People don’t understand that the audience looks at the other comic like, ‘What are you doing?’ Because you’re overshadowing this person. You have to volley back and forth, but you have to learn that it takes a minute. You have to learn that in the game, and you have to work to know that. Sometimes when you get a shot, just jump in. Comics will just jump in, but they don’t understand the formula.
Happy Gilmore 2 is now streaming on Netflix. To learn more about Kym Whitley, check out our full interview in the video above.
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