2015–2017: Breakthrough as Spider-Man
Holland appeared in four episodes of BBC Two's historical mini series Wolf Hall (2015), as Gregory Cromwell, son of the protagonist Thomas Cromwell played by Mark Rylance. He directed Tweet (2015), a three-minute short film about a young man building a birdhouse with his grandfather; Holland later expressed an interest in directing feature films in his 40s. Also in 2015, Holland co-starred as the teenage sailor Thomas Nickerson in Ron Howard's historical adventure-drama In the Heart of the Sea. The film is based on the namesake 2000 non-fiction book about the sinking of the American whaling ship Essex in 1820. In preparation, he and co-stars, including Chris Hemsworth, lost significant weight, consuming 500–1,000 calories a day. Holland performed most of his stunts in the film. In the Heart of the Sea received mixed reviews from critics, and grossed $93 million against a $100 million budget. Brian Truitt of the USA Today wrote that Holland "does a good job".
In June 2015, Holland signed a six-picture deal with Marvel Studios to play a teenage Peter Parker / Spider-Man. Growing up, Holland was a fan of Spider-Man; he owned 30 costumes and bed sheet covers of the character. He auditioned against 1,500 teenagers worldwide, including English actors Charlie Rowe and Asa Butterfield. While producers Kevin Feige and Amy Pascal were impressed with his performances in The Impossible, Wolf Hall, and In the Heart of the Sea, directors the Russo brothers cited Holland's dancing and gymnastics background as the reasons to cast him. Stan Lee, Spider-Man's creator, said Holland was the "exact age and height" when he envisioned the character. As part of the Marvel Cinematic Universe (MCU), he first appeared as Spider-Man in Captain America: Civil War (2016). The film was a critical and commercial success, grossing over $1.1 billion worldwide against a budget of $250 million to become the highest-grossing film of 2016. In a review for The Guardian, Peter Bradshaw praised Holland and co-star Paul Rudd (who played Ant-Man) as "seductively high-spirited and hilarious", and Richard Roeper of Chicago Sun-Times wrote that he made "a strong first impression" as Spider-Man.
In 2016, Holland co-starred with Joel Kinnaman and Percy Hynes White in the psychological thriller Edge of Winter. It was the first film he did without his parents' knowledge. Frank Scheck of The Hollywood Reporter found Holland and White "excellent", describing their terrified reaction as "more emotionally wrenching than the tired thriller genre conventions to which the film ultimately succumbs". At the 70th British Academy Film Awards in 2017, Holland won the Rising Star Award. Holland's first work that year was alongside Charlie Hunnam in James Gray's drama The Lost City of Z, which was released to positive reviews. On his last day of filming, he broke his nose after a failed backflip attempt. Holland played the son of Percy Fawcett (Hunnam), an explorer who makes several attempts to find a supposed lost ancient city in the Amazon rainforest. Neil Soans of The Times of India praised Holland for making the film emotional towards the end and Rex Reed of The New York Observer found him "remarkably strong and self-assured". Later in 2017, Holland played Samuel Insull in Alfonso Gomez-Rejon's The Current War, which received negative reviews and was a box-office failure. Clarisse Loughrey of The Independent found Holland's role insubstantial.
Holland's second film in 2017 was his solo feature as the title character in Spider-Man: Homecoming. As a result, Holland earned an entry in Guinness Book of World Records as the youngest actor to play a title role in the MCU. Though Holland took some inspiration from previous Spider-Man actors Tobey Maguire and Andrew Garfield, he wanted to add some newness in his reinterpretation of the character. Homecoming focused on Parker, as he tries to balance being a high-school student and a superhero. To prepare, Holland attended The Bronx High School of Science in the Bronx for a few days, although other students did not believe he was cast as Spider-Man. Holland felt this situation reflected the film's story, in which other characters are unaware that Parker is Spider-Man. Homecoming and Holland's performance received positive reviews. Peter Travers called it "a star performance given by a born actor". Made on a budget of $175 million, the film grossed over $800 million worldwide. Holland's final role in 2017 was in the Irish film Pilgrimage, which premiered at the Tribeca Film Festival. Outside film that year, Holland appeared with Zendaya on Paramount Network's Lip Sync Battle, during which he performed Rihanna's "Umbrella" in drag. His parents founded The Brothers Trust, a charitable organisation, which aims to use his popularity to raise funds for humanitarian causes.