Cadillac Rainbow

*Cadillac Rainbow is a ten-episode premium cable television drama series that originally aired in 2011 and 2012. Created by Terence Winter and Matthew Weiner, the series acts as a prequel to the critically acclaimed HBO drama The Sopranos, which ran for six seasons from 1999 to 2007. Cadillac Rainbow shares thematic and stylistic similarities with its predecessor, as well as drawing comparisons to the AMC series Better Call Saul, a prequel to Breaking Bad, for its exploration of the formative years of characters later depicted in The Sopranos*.

Set primarily in North Caldwell, New Jersey, and encompassing the years 1987 to 1992, Cadillac Rainbow delves into the burgeoning criminal career of Richard "Dickie" Moltisanti, the father of Christopher Moltisanti, a central figure in The Sopranos. The series portrays Dickie not as the revered, almost mythical figure Christopher often invokes, but as a complex and flawed individual navigating the treacherous landscape of organized crime within the DiMeo crime family during a period of significant upheaval and transition. The narrative also interweaves the early lives of several other characters who would become prominent figures in The Sopranos, offering glimpses into their formative experiences and the events that shaped their destinies. Critics and audiences lauded Cadillac Rainbow for its rich character development, intricate plotting, and its nuanced portrayal of Italian-American mob culture in the late 20th century.

Episodes

Season 1 (2011-2012)

1. "The Velvet Commode"

The series premiere, "The Velvet Commode," introduces Richard "Dickie" Moltisanti (portrayed by Alessandro Nivola) in 1987, as a mid-level associate within the DiMeo crime family, operating under the tutelage of his father, Aldo Moltisanti (Robert De Niro in a recurring role). Dickie, a charismatic but impulsive young man, is attempting to carve out his own niche within the family's waste management rackets, but his ambitions are often hampered by his father's old-school sensibilities and the ever-present shadow of his uncle, Pat Blundetto (Ray Liotta), a powerful and unpredictable capo.

The episode opens with a lavish christening party at the fictional Villa Bellagio, a catering hall in West Orange, New Jersey, for Aldo Moltisanti's newborn grandson. The opulent setting, complete with an ice sculpture of a cornucopia and a ten-piece band playing Italian folk tunes, masks simmering tensions beneath the surface. Dickie, eager to impress his father and Uncle Pat, proposes a new scheme involving infiltrating the burgeoning market of private sanitation contracts in the rapidly developing suburbs of Morris County. Aldo, wary of attracting unwanted attention from law enforcement, initially dismisses the idea, preferring to stick to established territories and methods. Pat Blundetto, however, sees potential in Dickie's initiative and subtly encourages him to pursue it, creating a rift between father and son.

Meanwhile, a parallel storyline introduces a young Janice Soprano (Alexandra Daddario), Tony Soprano's older sister, as a rebellious teenager struggling with her mother Livia's (Edie Falco, reprising her role in flashbacks) suffocating control. Janice, drawn to the allure of counterculture and the burgeoning punk rock scene in Hoboken, begins to associate with a group of older, disreputable figures, much to Livia's consternation. In one scene, Janice shoplifts a copy of Horses by Patti Smith from a record store in Greenwich Village, demonstrating her rebellious streak. Livia, in a conversation with her neighbor, refers to Janice's behavior as "disrespectful" and "unbecoming of a young lady," highlighting the generational clash in values.

The episode culminates in a tense confrontation at the "velvet commode"—a euphemism for a high-end nightclub in Newark that the DiMeo family uses as a discreet meeting place. Dickie, having defied his father's orders and secured a lucrative sanitation contract through aggressive, borderline illegal tactics, presents his success to Aldo and Pat. While Pat Blundetto praises Dickie's initiative, Aldo expresses disappointment in his son's methods, warning him about the dangers of unchecked ambition and the importance of loyalty within the family. The episode ends with Dickie, feeling both validated and chastised, staring out at the neon-lit cityscape of Newark, contemplating his future within the DiMeo organization.

2. "The Bust Out Tariff"

"The Bust Out Tariff" focuses on the escalating tensions between the DiMeo crime family and a rival crew from Philadelphia, led by the ruthless Angelo Bruno Jr. (Fisher Stevens), son of the infamous Philadelphia mob boss Angelo Bruno. The conflict arises from a dispute over a lucrative construction project at the Meadowlands Sports Complex, specifically the expansion of Giants Stadium to accommodate the upcoming 1994 FIFA World Cup. Both families see the project as a potential goldmine for skimming profits and securing no-show jobs for their associates.

Dickie Moltisanti, tasked by Pat Blundetto to secure the DiMeo family's stake in the project, finds himself directly clashing with Bruno Jr.'s crew, who are known for their violent and uncompromising tactics. The episode highlights the contrast in styles between the two organizations: the DiMeo family, while certainly capable of violence, generally prefers a more subtle and business-oriented approach, whereas Bruno Jr.'s crew operates with a more overtly aggressive and intimidatory style, reflecting the Philadelphia mob's reputation for brutality.

A key plot point revolves around the "bust out tariff"—a form of extortion where mobsters demand a percentage of profits from legitimate businesses under threat of sabotage or violence. Bruno Jr.'s crew attempts to impose an exorbitant bust out tariff on a trucking company contracted for the Giants Stadium expansion, threatening to disrupt deliveries of construction materials if their demands are not met. Dickie, under pressure from Pat Blundetto to resolve the situation without resorting to outright warfare, attempts to negotiate with Bruno Jr., but finds him intransigent and openly contemptuous of the DiMeo family's perceived weakness.

Meanwhile, a subplot explores the early relationship between Junior Soprano (Dominic Chianese, reprising his role in a younger iteration) and his nephew, Tony Soprano (Michael Gandolfini, son of James Gandolfini, in a poignant casting choice). Junior, a rising figure within the DiMeo family's ranks, takes a young and impressionable Tony under his wing, introducing him to the intricacies of the family business. In one scene, Junior takes Tony to a social club in Belleville and explains the concept of "omertà," the code of silence, emphasizing its importance for survival in their world. Tony, fascinated and somewhat intimidated by his uncle's authority, begins to absorb the lessons of loyalty and discretion that will shape his future trajectory. The episode concludes with a violent confrontation at a construction site in East Rutherford, where Dickie and his crew clash with Bruno Jr.'s men, resulting in property damage and several injuries, escalating the conflict between the two families to a dangerous level.

3. "Pigeon Fever"

"Pigeon Fever" delves into the world of illegal gambling and animal fighting, showcasing the DiMeo family's involvement in these lucrative but morally ambiguous enterprises. The episode centers on a high-stakes pigeon race circuit that operates throughout northern New Jersey and Pennsylvania, attracting a diverse clientele of gamblers and animal enthusiasts. Dickie Moltisanti, seeking to diversify his income streams and impress Pat Blundetto, becomes involved in managing a pigeon racing operation, partnering with a seasoned but ethically questionable pigeon breeder named Sal Demarco (Stanley Tucci).

The episode explores the subculture of pigeon racing, detailing the meticulous training regimes, specialized diets, and performance-enhancing drugs used to prepare pigeons for competition. Sal Demarco introduces Dickie to the darker aspects of the sport, including the practice of "Pigeon doping"—illegally administering stimulants to enhance a pigeon's speed and endurance. Dickie, initially hesitant about these unethical practices, is gradually drawn into the morally gray world of competitive pigeon racing as he witnesses the potential for significant financial gains. The term "pigeon fever," in this context, refers to the obsessive and addictive nature of gambling and the lengths to which individuals will go to win, even resorting to cruelty and illegal activities.

In a parallel storyline, the episode introduces a young Paulie "Walnuts" Gualtieri (Tony Sirico, reprising his role in flashback sequences, with his real-life son Richard Sirico playing the younger Paulie). Paulie, a street-smart and fiercely loyal associate of the DiMeo family, is depicted working as a debt collector and enforcer in Newark's Italian-American neighborhoods. The episode showcases Paulie's volatile temper and his propensity for violence, even in seemingly minor disputes. In one scene, Paulie violently confronts a deli owner in Bloomfield who is behind on his protection payments, demonstrating his ruthlessness and unwavering adherence to the demands of the DiMeo organization. This episode further establishes Paulie's character as a loyal but unpredictable enforcer, a trait that will become a defining characteristic in The Sopranos. The episode culminates in a dramatic pigeon race finale at a rural location in Sussex County, where Dickie's doped pigeons win, but at a cost. Sal Demarco is later revealed to be cooperating with law enforcement, providing evidence of illegal pigeon doping and gambling activities, leading to a raid and several arrests, including Dickie's.

4. "The Maniscalco Method"

"The Maniscalco Method" shifts focus to the financial underpinnings of the DiMeo crime family, exploring their sophisticated money laundering operations and their connections to legitimate businesses. The episode introduces Anthony "Beansie" Maniscalco (Steve Buscemi), a meticulous and shrewd accountant who serves as the DiMeo family's primary money launderer. Beansie, a seemingly unassuming figure, operates a network of shell corporations and offshore accounts to conceal the family's illicit profits from gambling, extortion, and drug trafficking. The "Maniscalco Method," as it is referred to within the family, is a complex and highly effective system of financial manipulation that allows the DiMeo organization to operate with relative impunity.

Dickie Moltisanti, facing mounting legal troubles from the pigeon racing scandal, is forced to rely on Beansie's expertise to navigate the complex financial implications of his arrest and potential prosecution. Beansie, initially reluctant to get involved in Dickie's personal problems, is persuaded by Pat Blundetto to assist him, highlighting the importance of family loyalty and solidarity within the organization. The episode delves into the intricacies of money laundering, showcasing Beansie's use of "smurfing"—breaking large sums of cash into smaller deposits to evade bank reporting requirements—and his utilization of front businesses, such as car dealerships and restaurants, to legitimize illicit funds.

A subplot introduces a young Artie Bucco (John Magaro), Tony Soprano's childhood friend and aspiring restaurateur. Artie, working as a line cook at a struggling Italian restaurant in Passaic, dreams of opening his own upscale establishment. He seeks financial backing from his uncle, a local businessman with ties to the DiMeo family, unaware of the potential dangers of associating with organized crime. Artie's naiveté and ambition make him vulnerable to exploitation, foreshadowing his later entanglements with Tony Soprano and the DiMeo family in The Sopranos. The episode concludes with Beansie successfully maneuvering Dickie's finances to mitigate the legal damage from the pigeon racing case, demonstrating the effectiveness of the "Maniscalco Method" and Beansie's invaluable role within the DiMeo organization. However, Beansie warns Dickie about the increasing scrutiny from federal law enforcement agencies, hinting at the growing challenges facing organized crime in the late 1980s.

5. "Eggplant Friday"

"Eggplant Friday" explores the cultural traditions and social rituals within the Italian-American community in North Caldwell, juxtaposing them with the darker aspects of mob life. The episode revolves around the annual Feast of Saint Gennaro, a vibrant street festival in Little Italy, Manhattan, that serves as a backdrop for both familial celebrations and clandestine criminal activities. "Eggplant Friday" refers to a specific tradition within the Moltisanti family, where every Friday during Lent, they abstain from meat and prepare a large, elaborate eggplant parmesan dish, a symbol of their Catholic faith and Italian heritage.

The episode opens with the Moltisanti family preparing for their annual pilgrimage to the Feast of Saint Gennaro. Aldo Moltisanti, despite his gruff exterior, is deeply invested in preserving Italian-American traditions and sees the feast as an opportunity to reconnect with his cultural roots and reinforce family bonds. Dickie, while less overtly sentimental than his father, also participates in the rituals, albeit with a degree of cynicism. The episode interweaves scenes of the vibrant street festival—with its food vendors, religious processions, and lively atmosphere—with more somber scenes depicting the DiMeo family conducting business meetings and settling scores amidst the festive crowds.

A subplot introduces a young Adriana La Cerva (Dominique Fishback), Christopher Moltisanti's future fiancée, as a high school student in West Essex, working part-time at a bakery in Caldwell. Adriana, depicted as intelligent and ambitious, dreams of escaping the confines of her working-class background and pursuing a career in the music industry. She encounters Dickie Moltisanti at the bakery, where he is picking up pastries for the Feast of Saint Gennaro, and there is an immediate spark of attraction between them, foreshadowing their later, more complicated relationship. The episode hints at the social and economic disparities within the Italian-American community, with Adriana representing a younger generation striving for upward mobility, while the Moltisantis embody a more established, albeit morally compromised, segment of that community. The episode culminates in a dramatic confrontation at the Feast of Saint Gennaro, where a rival faction attempts to disrupt the DiMeo family's operations, leading to a chaotic street brawl amidst the festival crowds, blurring the lines between celebration and violence.

6. "Guttata Spill"

"Guttata Spill" delves into the DiMeo crime family's involvement in illegal waste disposal and environmental crime, highlighting the ethical compromises and long-term consequences of their illicit activities. The "guttata spill" refers to a fictional incident involving the illegal dumping of toxic waste into the Passaic River, a real-world river that has suffered from significant industrial pollution. The episode explores the DiMeo family's exploitation of lax environmental regulations and their willingness to prioritize profit over public health and ecological well-being.

Dickie Moltisanti, tasked by Pat Blundetto to oversee the family's waste disposal operations, becomes increasingly aware of the environmental damage caused by their illegal dumping practices. He witnesses firsthand the devastating effects of toxic waste on local ecosystems and the potential health risks to communities living near the dumping sites. The episode draws parallels to real-world environmental disasters, such as the Love Canal disaster and the ongoing pollution of the Passaic River, raising awareness about the social and environmental costs of organized crime.

A subplot introduces a young Dr. Jennifer Melfi (Julianna Margulies, playing a younger version of Lorraine Bracco's character in flashbacks), as a psychology resident at a hospital in Newark. Jennifer, idealistic and committed to social justice, becomes involved in community outreach programs in underprivileged neighborhoods, witnessing the disproportionate impact of environmental pollution on marginalized communities. She encounters Dickie Moltisanti at a community health clinic in Newark, where he is seeking treatment for a minor injury sustained during a waste disposal operation. Their interaction is brief but sets the stage for their later, more significant encounter in The Sopranos. The episode highlights the ethical and moral dilemmas faced by individuals caught in the web of organized crime, contrasting Dickie's growing unease with the environmental consequences of his actions with the ruthless pragmatism of figures like Pat Blundetto, who prioritize profit above all else. The episode concludes with a covert investigation by the Environmental Protection Agency (EPA) into the "guttata spill," hinting at the increasing legal and regulatory pressures facing the DiMeo family's illicit operations.

7. "The Book of Calandra"

"The Book of Calandra" delves into the history and traditions of the DiMeo crime family, exploring the origins of their power and influence in northern New Jersey. "The Book of Calandra" is a fictional, hand-written ledger passed down through generations of the Calandra family, the original founders of the crime family that would later become the DiMeo organization. The book contains a detailed record of the family's early operations, including their involvement in bootlegging during Prohibition, their expansion into labor racketeering and gambling in the mid-20th century, and the key figures who shaped their rise to prominence.

Aldo Moltisanti, custodian of "The Book of Calandra," becomes increasingly concerned about the future of the family and the erosion of traditional values in the face of modern pressures and temptations. He sees Dickie's ambition and impulsiveness as a threat to the family's legacy and attempts to instill in him a deeper appreciation for the history and traditions enshrined in "The Book of Calandra." The episode features flashbacks to earlier periods in the DiMeo family's history, depicting key moments and figures from their past, providing context for the current conflicts and challenges facing Dickie and his contemporaries.

A subplot explores the early career of Silvio Dante (Steven Van Zandt, reprising his role in flashback sequences, with his son Dante Van Zandt playing young Silvio). Silvio, a childhood friend of Dickie Moltisanti and a natural peacemaker, is depicted working as a manager at a local music club in Asbury Park, a town known for its vibrant music scene. Silvio's skills in negotiation and conflict resolution are evident even in his early years, foreshadowing his later role as Tony Soprano's consigliere. He attempts to mediate a dispute between Dickie and a rival crew over territorial rights in Asbury Park, demonstrating his ability to navigate complex social dynamics and defuse potentially violent situations. The episode emphasizes the importance of history and tradition in shaping the identity and culture of the DiMeo crime family, while also highlighting the challenges of adapting to changing times and maintaining relevance in a rapidly evolving world. The episode concludes with Aldo entrusting "The Book of Calandra" to Dickie, urging him to learn from the past and become a responsible steward of the family's legacy.

8. "Nine-Hole Punch"

"Nine-Hole Punch" focuses on the seemingly mundane but often critical aspects of organized crime, highlighting the importance of bureaucratic efficiency and attention to detail in maintaining a successful criminal enterprise. The "nine-hole punch" refers to a specific method of accounting and record-keeping used by the DiMeo family to track their various rackets and ensure accurate distribution of profits. The episode underscores the contrast between the glamorous image of mob life often portrayed in popular culture and the reality of tedious paperwork, meticulous accounting, and the constant need for vigilance against both law enforcement and internal betrayal.

Dickie Moltisanti, initially dismissive of the seemingly trivial administrative tasks associated with the family business, is forced to confront the consequences of neglecting these details when a discrepancy is discovered in the "nine-hole punch" records, leading to suspicion of embezzlement within the ranks. Beansie Maniscalco, the family's meticulous accountant, plays a central role in uncovering the accounting error and identifying the potential culprit. The episode showcases Beansie's expertise in financial forensics and his unwavering commitment to accuracy and accountability, even in the morally ambiguous world of organized crime.

A subplot introduces a young Salvatore "Big Pussy" Bonpensiero (Vincent Pastore, reprising his role in flashback sequences, with his son Frankie Pastore playing young Pussy). Pussy, working as a mechanic at a garage in Elizabeth, is depicted as loyal and eager to prove himself to the DiMeo family. He is tasked with transporting and securing sensitive documents related to the "nine-hole punch" system, demonstrating his trustworthiness and willingness to handle important responsibilities. However, the episode also hints at Pussy's financial vulnerabilities and his susceptibility to temptation, foreshadowing his later betrayal of Tony Soprano in The Sopranos. The episode emphasizes the importance of seemingly mundane tasks in maintaining the stability and profitability of a criminal organization, while also highlighting the ever-present threat of internal corruption and betrayal. The episode concludes with the discovery of the embezzler—a low-level associate driven by desperation—and the swift and brutal consequences that follow, reinforcing the DiMeo family's zero-tolerance policy towards disloyalty.

9. "The Cicero Gambit"

"The Cicero Gambit" explores the strategic maneuvering and political machinations employed by the DiMeo crime family to maintain their power and influence in the face of external threats. "The Cicero Gambit" is a fictional strategic maneuver, named after the Roman orator and statesman Marcus Tullius Cicero, involving a complex negotiation and alliance-building strategy to outmaneuver rivals and consolidate power. The episode focuses on the escalating conflict with Angelo Bruno Jr.'s Philadelphia crew and the DiMeo family's attempts to forge alliances with other crime families to counter Bruno Jr.'s aggression.

Pat Blundetto, recognizing the growing threat posed by Bruno Jr., orchestrates "The Cicero Gambit," initiating secret negotiations with the Genovese crime family in New York City, seeking their support in resolving the conflict with Philadelphia. The episode delves into the complex web of alliances and rivalries among the various Mafia families in the Northeast, highlighting the delicate balance of power and the constant jockeying for position. Dickie Moltisanti is tasked with acting as a liaison in the negotiations with the Genovese family, requiring him to navigate the treacherous world of inter-family politics and demonstrate his diplomatic skills.

A subplot introduces a young Carmela De Angelis (Mackenzie Davis), Tony Soprano's future wife, as a college student at Seton Hall University in South Orange, studying sociology and grappling with questions of faith and morality. Carmela, raised in a devout Catholic household, is increasingly questioning the values and beliefs she was brought up with, as she becomes exposed to different perspectives and social realities. She encounters Tony Soprano at a church picnic in West Orange, and their initial interaction is marked by intellectual sparring and mutual attraction, hinting at the complex and often contentious dynamic that will define their relationship in The Sopranos. The episode emphasizes the strategic and political dimensions of organized crime, showcasing the importance of alliances, negotiations, and power plays in maintaining dominance and resolving conflicts. The episode concludes with a tense summit meeting between representatives of the DiMeo, Genovese, and Philadelphia families, where "The Cicero Gambit" is put to the test, and the future of the conflict hangs in the balance.

10. "Open Veins of Newark"

The season finale, "Open Veins of Newark," brings the various storylines to a head, culminating in a violent confrontation that reshapes the power dynamics within the DiMeo crime family and sets the stage for future conflicts. "Open Veins of Newark" is a metaphorical reference to the city's history of industrial decay, social unrest, and underlying violence, suggesting that the city's troubled past is inextricably linked to the criminal underworld that thrives within it.

The episode opens with the fallout from the summit meeting, where "The Cicero Gambit" proves partially successful, securing the Genovese family's neutrality in the conflict but failing to fully resolve the tensions with Angelo Bruno Jr.'s Philadelphia crew. Bruno Jr., feeling betrayed and humiliated, launches a retaliatory strike against the DiMeo family, targeting key figures and assets. The episode depicts a series of escalating acts of violence, including bombings, arson, and targeted assassinations, plunging Newark and its surrounding suburbs into a state of fear and uncertainty.

Dickie Moltisanti, caught in the crossfire of the escalating violence, is forced to make difficult choices that will have lasting consequences for his future and his relationships within the family. He witnesses firsthand the brutality and senselessness of mob warfare, and begins to question his own involvement in the criminal lifestyle. The episode also explores the personal toll of violence and the psychological impact on individuals caught in the web of organized crime. The episode culminates in a dramatic showdown at a warehouse district in Newark, where Dickie and his crew confront Angelo Bruno Jr. and his men in a bloody and chaotic gunfight. The outcome of the confrontation is ambiguous, leaving the fates of several key characters uncertain and setting the stage for a potential second season exploring the long-term repercussions of the Newark conflict and the evolving dynamics within the DiMeo crime family. The final scene depicts Dickie, wounded and emotionally drained, standing amidst the wreckage of the warehouse, staring out at the sprawling cityscape of Newark, the "open veins" of the city reflecting the violence and corruption that run deep beneath its surface.

Cast and Characters

• Alessandro Nivola as Richard "Dickie" Moltisanti
• Robert De Niro as Aldo Moltisanti
• Ray Liotta as Pat Blundetto
• Edie Falco as Livia Soprano (flashbacks)
• Dominic Chianese as Junior Soprano
• Michael Gandolfini as Young Tony Soprano
• Tony Sirico as Paulie "Walnuts" Gualtieri (flashbacks)
• Richard Sirico as Young Paulie "Walnuts" Gualtieri
• Steve Buscemi as Anthony "Beansie" Maniscalco
• John Magaro as Artie Bucco
• Dominique Fishback as Young Adriana La Cerva
• Julianna Margulies as Young Dr. Jennifer Melfi (flashbacks)
• Steven Van Zandt as Silvio Dante (flashbacks)
• Dante Van Zandt as Young Silvio Dante
• Vincent Pastore as Salvatore "Big Pussy" Bonpensiero (flashbacks)
• Frankie Pastore as Young Salvatore "Big Pussy" Bonpensiero
• Mackenzie Davis as Young Carmela De Angelis
• Fisher Stevens as Angelo Bruno Jr.
• Stanley Tucci as Sal Demarco

Reception

Cadillac Rainbow received critical acclaim upon its release, with many praising its nuanced character development, intricate plotting, and faithful recreation of the world of The Sopranos. Alessandro Nivola's portrayal of Dickie Moltisanti was particularly lauded, with critics noting his ability to capture the character's charisma, impulsiveness, and underlying vulnerability. The series was also praised for its exploration of the social and cultural context of Italian-American mob life in the late 1980s and early 1990s, as well as its thematic resonance with The Sopranos, exploring themes of family, loyalty, ambition, and the corrupting influence of power. Some critics, however, noted that the series, while well-crafted, lacked the groundbreaking originality of The Sopranos, and that it occasionally relied too heavily on callbacks and references to its predecessor. Despite these minor criticisms, Cadillac Rainbow was widely considered a successful and worthy prequel, deepening the mythology of The Sopranos and offering a compelling exploration of the formative years of its iconic characters. The series garnered numerous awards and nominations, including multiple Primetime Emmy Awards and Golden Globe Awards. While only one season was produced, the critical and audience success of Cadillac Rainbow solidified its place as a significant entry in the television drama landscape of the early 2010s and further cemented the legacy of The Sopranos franchise.