“Monday” follows the start of a typical Saturday Night Live production week, offering a behind-the-scenes look at Michaels’s leadership style and the pressures of mounting a live show. The chapter begins with Michaels attending a tea for Tom Stoppard and managing a crisis involving a death threat against Jimmy Fallon. It moves into Monday’s Topical Meeting, where Michaels and his senior staff brainstorm ideas in the lead-up to the week’s show, hosted by Jonah Hill. Throughout the chapter, the narrative highlights Michaels’s balancing act: smoothing over cast tensions, navigating political sensitivities, and maintaining the show’s comedic identity amid shifting cultural and political winds. The chapter also provides rich characterization of Michaels himself—his dry humor, ritualistic leadership style, and mythic standing among the comedy world—as well as insight into how Monday pitch meetings function more to set tone and morale than to finalize content.

This chapter explores Michaels’s early life in Toronto, highlighting the family, community, and cultural influences that shaped him. Raised in a Jewish household filled with both affection and anxiety, Lorne was exposed early to the world of entertainment through his grandparents’ movie theater and his family’s love of film and television. His mother’s intense personality and his father’s quieter presence left a lasting impression, particularly after his father’s death when Lorne was 14—a loss that profoundly impacted his emotional development and leadership style. During adolescence, Lorne immersed himself in American television, discovered his passion for comedy, and began writing and directing school revues. Mentorships with figures like Frank Shuster of Wayne and Shuster fame helped hone his understanding of comedic structure. This period instilled in Lorne both a deep love for performance and a persistent, vigilant drive that would later define his career in show business.

After returning from London in 1966, Michaels reconnected with Hart Pomerantz to form a two-man comedy team, performing in Toronto clubs and eventually securing regular appearances on CBC radio. Their act, “Lipowitz and Pomerantz,” combined political satire and character-driven humor, culminating in a signature bit featuring a Canadian Beaver character. Although they briefly found success, their style felt increasingly outdated to Michaels, who grew more drawn to the counterculture and avant-garde film scene. His work with experimental cinema groups and the ambitious but financially disastrous Cinethon festival shifted his creative ambitions toward directing. Meanwhile, Michaels and Pomerantz landed a meeting with Woody Allen through their William Morris agent, though the collaboration did not yield material for Allen. As his marriage to Rosie Shuster began, Michaels officially changed his name from Lipowitz to Michaels, solidifying his commitment to a professional career in entertainment. A job offer from Hollywood soon beckoned.

In 1968, Michaels and Hart Pomerantz arrived in Los Angeles to write for The Beautiful Phyllis Diller Show, but quickly discovered its humor and production style were outdated. Though the show briefly outperformed Barbra Streisand’s A Happening in Central Park, ratings soon fell, and the show was canceled. Michaels networked with industry veterans, gained insight into the mechanics of television production, and was eventually hired to write monologue jokes for Laugh-In, NBC’s hit sketch show. Despite the program’s success, Michaels found the work creatively unsatisfying and disconnected, with jokes rewritten or aired without attribution. He envied younger, more politically engaged writers like those on The Smothers Brothers Comedy Hour. After one season, Michaels and Pomerantz were let go. Though disillusioned, Michaels returned to Toronto with deeper experience, valuable contacts, and a firmer sense of the kind of show business career he wanted to build—one that balanced mass appeal with cultural relevance and creative control.

Returning to Toronto after Laugh-In, Michaels and Hart Pomerantz were celebrated as rising comedy talents and signed to an ambitious CBC contract to create a series of specials. Michaels took the lead in producing the shows, bringing in friends like Rosie Shuster, Andrea Martin, and Dan Aykroyd. Their work, beginning with That’s Canada for You and culminating in The Hart and Lorne Terrific Hour, blended satire, music, and conceptual humor but drew mixed critical responses. Michaels, increasingly focused on producing rather than performing, developed skills in editing and managing creative teams. Despite modest success, the CBC abruptly canceled the series. Disillusioned by limited opportunities in Canada, Michaels seriously considered offers to return to Hollywood. The chapter ends by describing how Michaels parted ways with Pomerantz, marking a key turning point as he prepares to move toward a larger stage and greater creative autonomy in the United States.