Ryan Reynolds

Two Guys and a Girl

Reynolds landed his first major role in the ABC sitcom Two Guys and a Girl, which ran for four seasons. This steady television work provided him with financial stability and industry recognition, though he remained relatively unknown outside of TV circles.

Van Wilder Breakthrough

The comedy National Lampoon's Van Wilder became a cult hit and showcased Reynolds' comedic timing. The film's success helped him transition from television to film, though he was still building his movie star credentials.

The Proposal Success

Starring opposite Sandra Bullock in The Proposal, which grossed over $317 million worldwide, established Reynolds as a viable romantic comedy lead. This box office success significantly increased his asking price and mainstream appeal.

Green Lantern Disappointment

Despite landing the lead role in DC's Green Lantern with a major payday, the film was a critical and commercial failure. However, he met his future wife Blake Lively on set, and the experience later informed his approach to Deadpool.

Deadpool Phenomenon

After years of passionate development, Deadpool became a cultural phenomenon, grossing $782 million worldwide on a modest budget. Reynolds' performance and producing role transformed him into a bonafide A-list star and gave him creative control over future projects.

Deadpool 2 and Aviation Gin

Deadpool 2 continued the franchise's success with $785 million globally, while Reynolds' acquisition of Aviation American Gin began his transformation into a savvy entrepreneur. His marketing prowess became evident through viral Aviation Gin campaigns.

Aviation Gin Sale

Reynolds sold Aviation Gin to Diageo for up to $610 million, with his stake reportedly earning him over $120 million. This deal cemented his reputation as a brilliant businessman beyond his acting career, making him one of Hollywood's wealthiest stars.

Wrexham AFC Acquisition

Reynolds and Rob McElhenney purchased Wrexham AFC, creating the hit documentary series Welcome to Wrexham. This venture expanded his global brand and demonstrated his ability to turn unconventional investments into cultural moments.

Deadpool & Wolverine Blockbuster

Deadpool & Wolverine became the highest-grossing R-rated film of all time with over $1.3 billion worldwide. Reynolds' producer and star roles, combined with backend deals, generated massive profits and solidified his position as a top-tier Hollywood power player.

Entertainment Empire Status

Reynolds maintains A-list status through his combination of blockbuster acting, producing, and business ventures including Mint Mobile (sold for $1.35 billion) and Maximum Effort Productions. He is one of Hollywood's most bankable and business-savvy stars, commanding massive fees and backend deals.