Dream Breaker: A Pickleball Story" - How a Hollywood Director Captured the Birth of a Professional Sport
Ashley Underwood's Documentary Offers an Insider's Look at Pickleball's Explosive Growth and the Characters Shaping Its Future
In the world of sports documentaries, few subjects offer the combination of rapid growth, quirky culture, and high-stakes drama quite like the rise of professional pickleball. Enter Ashley Underwood, a Hollywood director who found herself unexpectedly drawn into the world of this paddle sport phenomenon. What started as a casual introduction to the game during the pandemic has culminated in "Dreambreaker: A Pickleball Story," a feature-length documentary that captures the birth of a professional sport in real-time.
Underwood's film takes viewers on a whirlwind journey through the early days of professional pickleball, offering unprecedented access to the players, league owners, and behind-the-scenes power brokers who are shaping the future of the sport. "Dream Breaker" chronicles the growing pains, triumphs, and unexpected twists that come with turning a recreational pastime into a full-fledged professional league.
In a recent interview with Mike "Sleeves" Sliwa on the Senior Pickleball Report podcast, Underwood offered insights into the making of the film, the challenges of documenting a rapidly evolving story, and the unique characters that make pickleball such a compelling subject. As the sport continues its meteoric rise, "Dream Breaker" stands as a testament to a pivotal moment in pickleball history, one that will never be repeated.
1. How did pickleball find you?, 2:22 Ashley Underwood's introduction to pickleball came through a friend during the COVID-19 pandemic. Initially a tennis player, Underwood was repeatedly invited to try pickleball at Memorial Park in Santa Monica. Her friend described it as a "happy place" where people from all walks of life came together to play. Intrigued by the diverse community and the joy it brought to players, Underwood decided to give it a shot. She quickly found herself enjoying the sport and its inclusive nature, playing regularly with a group of friends and their spouses. This personal connection to the game would eventually inspire her to explore pickleball's story on a much larger scale. 2. The decision to make a full feature film, 3:52 The leap from casual player to documentary filmmaker came through a combination of opportunity and intrigue. Underwood, who had a development job at the time, had access to funds for creating sizzle reels and proof-of-concept pitches. When executive producer Isabelle Thomas suggested making something about pickleball, Underwood saw potential. Her research led her to Craig Coin, who was writing one of the first major articles about pickleball for Vanity Fair, How Pickleball Won Over Everyone From Leonardo DiCaprio to Your Grandparents. Coin's extensive knowledge of the sport and its key players opened Underwood's eyes to the professional side of pickleball. Rather than creating a broad overview of the pickleball phenomenon, Underwood decided to focus on the emerging professional leagues and the players at the forefront of the sport's growth. This insider perspective would become the core of "Dream Breaker," offering viewers a unique look at the birth of a professional sport.
3. The challenge must have been "what to leave in and what to leave out" as well as access to people, 6:30 One of the biggest challenges in creating "Dream Breaker" was the ever-evolving nature of the story. Underwood and her team had to make constant decisions about what events to film, what storylines to follow, and how to allocate their limited resources. The sport was changing so rapidly that new developments were occurring almost daily, forcing the filmmakers to be nimble and adapt their approach on the fly. Access to key figures in the pickleball world also presented challenges. While initially open and welcoming, as more money and celebrity attention entered the sport, some players and league officials became more guarded. Underwood had to navigate the changing landscape of access, balancing the need for compelling footage with the desire of some subjects to control their own narratives. Despite these challenges, Underwood maintained her commitment to creative freedom, refusing to create branded content for any particular league and instead focusing on telling an authentic story of the sport's growth. 4. Professional Film Makers - Favorite part of the movie, 14:49 Underwood's background as a professional filmmaker allowed her to bring a level of expertise and polish to "Dream Breaker" that sets it apart from other pickleball content. Her experience working on projects with constantly changing scripts prepared her for the unpredictable nature of documenting a rapidly evolving sport. This professional approach is evident in the film's ability to balance the serious aspects of the emerging professional game with the quirky, colorful culture of recreational pickleball. One of the most beloved aspects of the film, according to Underwood, is the narration and commentary provided by Mike "Sleeves" Sliwa. His articulate and knowledgeable explanations of the sport's complexities, combined with his colorful personality, help make the film both informative and entertaining. Underwood credits Sliwa with helping to streamline complex information and adding a touch of humor that keeps the documentary engaging for viewers, regardless of their familiarity with pickleball. 5. Dreambreaker: A Pickleball Story. - The Beginning, Things were changing daily, 20:37 The creation of "Dream Breaker" was a rollercoaster ride for Underwood and her team, with the story constantly evolving as they filmed. One of the most dramatic moments came when they captured footage of Steve Kuhn and Julio Morejon in their New York City apartment, discussing the collapse of a potential merger and their plans to win back players. This scene, which Underwood describes as having a "Hollywood formula" quality, became a pivotal moment in the film's narrative. The unpredictable nature of the story meant that Underwood often had to make quick decisions about where to allocate resources and which events to film. The rapid changes in the professional pickleball landscape meant that what seemed like an ending one day could become the beginning of a new chapter the next. This constant state of flux added both excitement and stress to the filmmaking process, as Underwood and her team worked to capture the birth of a professional sport in real-time. 6. Tom Dundon, The empty chair, 26:30 One of the most elusive figures in the pickleball world was Tom Dundon, a key player in the sport's professional development. Throughout much of the filming process, Dundon declined to participate, citing his belief that the focus should be on the players rather than league owners. This presented a challenge for Underwood, as Dundon's influence on the sport was significant. In a dramatic turn of events, Underwood was finally able to secure an interview with Dundon near the end of the production. This last-minute addition to the film provides crucial context and perspective on the development of professional pickleball. Underwood's decision to visually introduce Dundon with a shot of an empty chair before he sits down creates a sense of anticipation and underscores his role as the "man behind the curtain" in the pickleball world. This interview helps to tie together many of the film's storylines and provides a satisfying conclusion to the documentary's narrative arc. 7. Filming off grid, 28:05 One of the most unique and challenging aspects of filming "Dream Breaker" was capturing footage of Mike "Sleeves" Sliwa at his off-grid location in rural New Mexico. This required careful planning and presented logistical challenges for Underwood and her crew. The remote location meant that the team had to be self-sufficient, bringing all necessary equipment and power sources with them. Despite the difficulties, these segments add a distinctive flavor to the film. The contrast between the polished, professional world of emerging pickleball leagues and Sliwa's rugged, off-grid lifestyle provides visual interest and helps to ground the story. It serves as a reminder of the sport's grassroots appeal and the diverse backgrounds of those involved in pickleball. Underwood credits her team's professionalism and adaptability for successfully capturing these important scenes in such a challenging environment. 8. The Ginger That Changed The Taste Of The Film, 32:31 The segments featuring Mike "Sleeves" Sliwa offer viewers a chance to step back and gain perspective on the larger pickleball culture beyond the professional circuit. The effectiveness of these scenes became apparent during film screenings, where Underwood observed audience reactions. She noted that viewers seemed to look forward to Sliwa's appearances throughout the film, appreciating the moments of levity and insight he provided. This balance between the serious business aspects of professional pickleball and the sport's more lighthearted, community-oriented side is key to the film's appeal, making it accessible and enjoyable for both hardcore pickleball fans and casual viewers alike.
9. Did I Need To Be In The Film, So Many Moving Parts, 34:24 Sliwa initially questioned his role in the film, wondering if his segments were necessary to the overall narrative. However, feedback from film industry professionals, including Underwood herself, confirmed the importance of his contributions. His segments were described as providing a necessary "ginger" effect, changing the palette of the film and offering viewers a chance to process the complex information presented about the professional pickleball world. Underwood emphasizes that Sliwa's articulate explanations of the sport's intricacies, combined with his colorful personality, help make the film more accessible and entertaining. His segments serve to break up the more intense moments of the professional storyline and remind viewers of pickleball's broader appeal. This balance was crucial in telling a comprehensive story about the sport's growth and culture. 10. Many Moving Parts, 35:51 The creation of "Dream Breaker" was a complex undertaking, with numerous moving parts that Underwood and her team had to juggle throughout the production process. The rapidly evolving nature of professional pickleball meant that new developments were constantly occurring, forcing the filmmakers to adapt their story and approach on the fly. Underwood credits her background in productions with constantly changing scripts for preparing her to handle the unpredictable nature of this project. The film required careful balancing of various elements: the emerging professional leagues, the recreational pickleball scene, the business aspects of the sport's growth, and the personal stories of key players. Coordinating film crews, securing interviews, and making decisions about which events to cover all added to the complexity of the production. Despite these challenges, Underwood and her team managed to create a cohesive narrative that captures the excitement and growing pains of a sport on the cusp of mainstream success. The film's ability to weave together these various threads into a compelling story is a testament to the skill and dedication of the filmmakers involved. 11. Outro, 37:03 As "Dream Breaker: A Pickleball Story" prepares for wider release, Underwood expresses pride in the final product and excitement for audiences to experience the film. The documentary stands as a unique snapshot of a pivotal moment in pickleball history, chronicling the sport's transition from a casual pastime to a professional endeavor with significant financial stakes.
Underwood encourages viewers to spread the word about the film once it becomes widely available, emphasizing its appeal to both pickleball enthusiasts and those unfamiliar with the sport. She also takes a moment to acknowledge the contributions of Sliwa and his friends, who wrote and performed the song that plays at the end of the film, adding another layer of authenticity to the project.
As "Dream Breaker" prepares to make its way to streaming services, it promises to offer viewers an inside look at the characters, conflicts, and passion driving pickleball's meteoric rise. For anyone interested in sports, entrepreneurship, or simply a good story, Underwood's film provides a fascinating glimpse into the birth of a new professional sport, captured in real-time by a skilled and dedicated team of filmmakers.
Time Code List
- 0:00 Intro
- 2:22 How did pickleball find you?
- 3:52 The decision to make a full feature film
- 6:30 The challenge must have been "what to leave in and what to leave out" as well as access to people
- 14:49 Professional Film Makers - Favorite part of the movie
- 20:37 Dreambreaker: A Pickleball Story. - The Beginning, Things were changing daily
- 26:30 Tom Dundon, The empty chair
- 28:05 Filming off grid
- 32:31 The Ginger That Changed The Taste Of The Film
- 34:24 Did I Need To Be In The Film, So Many Moving Parts
- 37:03 Outro
Serving Up History: 'Dream Breaker' Captures Pickleball's Pro Evolution
In the rapidly evolving world of sports, few stories are as compelling as the rise of professional pickleball. Director Ashley Underwood's documentary "Dream Breaker: A Pickleball Story" offers an unprecedented look at this phenomenon, chronicling the sport's transition from a casual pastime to capturing the attention of Wall Street. Through a combination of intimate access, expert storytelling, and a keen eye for the sport's unique culture, Underwood has created a film that captures a pivotal moment in pickleball history.
The genesis of "Dream Breaker" is as organic as the sport itself. Underwood, initially a tennis player, was introduced to pickleball during the COVID-19 pandemic. Intrigued by the diverse community and infectious enthusiasm surrounding the game, she quickly became a regular player. This personal connection to pickleball, combined with her background in film development, led Underwood to see the potential for a larger story.
Rather than creating a broad overview of the pickleball phenomenon, Underwood chose to focus on the emerging professional leagues, the Professional Pickleball Association (PPA) and Major League PIckleball (MLP), and the rivalry between two Texas billionaires, Steve Kuhn and Tom Dundon. This decision allowed her to dive deep into the complexities, challenges, and excitement of turning a recreational activity into a professional sport with significant financial stakes.
The creation of "Dream Breaker" was not without its challenges. The rapidly changing landscape of professional pickleball meant that new developments were occurring almost daily, forcing Underwood and her team to be nimble and adaptive in their approach. Access to key figures in the pickleball world also presented hurdles, as the influx of money and celebrity attention led some players and league officials to become more guarded.
Despite these obstacles, Underwood's commitment to creative freedom and authentic storytelling shines through in the final product. The film strikes a delicate balance between the serious business aspects of professional pickleball and the sport's more lighthearted, community-oriented side. This is achieved in part through the inclusion of segments featuring Mike "Sleeves" Sliwa, whose articulate explanations and colorful personality serve as a "palate cleanser" throughout the film.
One of the most dramatic elements of "Dream Breaker" is its real-time documentation of major events in the professional pickleball world. From capturing pivotal meetings in New York City apartments to securing a last-minute interview with influential figure Tom Dundon, the film offers viewers an insider's perspective on the sport's growing pains and triumphs.
The documentary also stands out for its production quality and professional approach. Underwood's experience in Hollywood productions is evident in the film's polished look and narrative structure. At the same time, the team's ability to adapt to challenging filming conditions, such as shooting in Sliwa's off-grid location in rural New Mexico, demonstrates their commitment to telling a comprehensive story.
As "Dream Breaker" prepares for wider release, it promises to appeal to both dedicated pickleball enthusiasts and those unfamiliar with the sport. The film offers a fascinating look at entrepreneurship, community building, and the birth of a new professional sport. It serves as a time capsule of sorts, preserving a unique moment in pickleball history that will never be repeated.
Underwood's pride in the final product is well-deserved. "Dream Breaker: A Pickleball Story" is more than just a sports documentary; it's a testament to the passion, dedication, and vision of those working to elevate pickleball to new heights. As the sport continues its meteoric rise, this film will stand as an important record of its early professional days, offering viewers an intimate look at the characters and conflicts that shaped pickleball's journey from community courts to national headlines.
For anyone interested in sports, business, or simply a good story, "Dream Breaker" provides a compelling narrative of ambition, community, and the unpredictable nature of creating something new. As pickleball continues to grow and evolve, this documentary will likely be remembered as a crucial document of the sport's pivotal transition, captured with skill and insight by Underwood and her team.
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