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While promoting his 2017 film Como se Tornar o Pior Aluno da Escola, Gentili allegedly incited attacks on the authors of negative reviews through his social networks. The CinePOP website accused the director of initiating a wave of virtual attacks.

In August 2016, filming began on Como se Tornar o Pior Aluno da Escola, an adaptation of Gentili's first book with Gentili as creator, producer and screenwriter. It was released in April 2017 to mostly negative reviews.

In February 2015, Gentili opened another stand-up venue, The Comedy Club in Orlando, Florida. Comedian Diogo Portugal [pt] joined as a partner in the venture.

Rede Bandeirantes filed a lawsuit to stop The Noite from airing at SBT. According to the broadcaster, Gentili had been contracted until 2015. The judge did not accept this, nor claims that the new show was plagiarized. In August 2015, Gentili was ordered to pay R$2 million for breach of agreement, the judge noting damages such as the loss of advertisers. Gentili appealed the ruling.

On 31 July 2015, Gentili posted a joke in his Twitter after the media announced an attack at Instituto Lula [pt] . The institution promised to seek justice. However, the judge rejected the lawsuit, noting that it was an "obvious joke" from the well-known comedian, and criticized the "unparalleled patrol of thought in Brazil."

With most of his team from Agora É Tarde, SBT launched Gentili's new late-night talk show, The Noite com Danilo Gentili (English: The Night with Danilo Gentili ) on 10 March 2014. The program exceeded the broadcaster's expectations, doubling its audience in that time slot. Critics praised the show, which they said was on the same level as U.S. late shows.

Gentili also produced and hosted the 2014 series Politicamente Incorreto [pt] on FX Brasil.

In June 2014, Alberto Cantalice, vice president of Partido dos Trabalhadores, put Gentili on a blacklist called "A desmoralização dos pitbulls da grande mídia" (English: Demoralizing the mainstream media pitbulls ) published on the Workers' Party's official website. The list also included Marcelo Madureira, Lobão, Arnaldo Jabor, Reinaldo Azevedo, Diogo Mainardi, Guilherme Fiuza [pt] and Demétrio Magnoli, accusing them of elitism, being against the poor and for hate speech.

Gentili had his film acting debut in Mato sem Cachorro which premiered at the 2013 Rio de Janeiro Film Festival. According to critic Raphael Max, Gentili brought laughs to every scene shared with his co-star.

Financial difficulties at Rede Bandeirantes brought cuts to Agora É Tarde in December 2013 and a scale-back of comedy specials. Amid speculation of dissatisfaction by Gentili, he was bought out of his contract by Sistema Brasileiro de Televisão (SBT).

By the end of October 2013, Gentili and Marcelo Mansfield were charged with injury by Michele Rafaela Maximino, a nurse and human milk donor, due to a joke made by them on Agora É Tarde broadcast on 3 October. The donor had been entered into the Guinness World Records by donating 300 litres (66 imp gal; 79 US gal) of milk and she alleged the joke had caused her to be bullied in her home town, which caused her to stop donating milk. The justice of Pernambuco ruled that Rede Bandeirantes pay damages of R$5,000 for every day the joke remained on their website.

Despite doubts from the mainstream media, the show received excellent ratings for its time slot and was expanded from two to three nights per week. Newspaper O Globo named Agora É Tarde the best TV show of the year and Gentili the best TV show host. It was also chosen by the Brazilian Press Association as the 'Best Talk Show' in the 2012 edition of their awards.

In June 2012, Gentili's third book, A Vida e Outros Detalhes Insignificantes [pt] (English: Life and Other Insignificant Details ), was published. It related his family's customs and details of old relationships mixed with ideas from his stand-up shows.

He gained national recognition on the TV show Custe o Que Custar (CQC), aired on the Band network. Gentili then created and hosted Agora É Tarde (2011–2013), a late-night talk show on the same network, later moving to the SBT network with talk show The Noite com Danilo Gentili (2014–present). Gentili is also a partner in two stand-up comedy clubs, has written four books, and has acted in, written and produced films. He was convicted and sentenced to seven months of prison time in April 2019 for defaming a Brazilian federal congresswoman with a suggestion that she was a "puta", or prostitute, in a YouTube video.

In October 2011, Gentili hosted eight episodes of Comedy Central Apresenta [pt] , originally shown on VH1 Brasil to promote the launch of Comedy Central Brasil. Recorded at Comedians Comedy Club, the shows featured showcase performances by stand-up comedians.

During the 2010–11 season of CQC, Gentili also featured in the segments "Proteste Já" (English: Protest Now ) and "National Identity" as well as other comedic pieces commenting on national political events.

In August 2010, Gentili partnered with Rafinha Bastos and Ítalo Gusso to found Comedians Comedy Club, at Rua Augusta in São Paulo. It was among the first clubs in Brazil dedicated to stand-up comedy.

The day before Brazil's 2010 presidential election, with a television ban on political humour, Gentili released Politicamente Incorreto [pt] (English: Politically Incorrect ) on the Internet. This stand-up show was written and performed by Gentili, in which he spoke of every presidential candidate that year. It was streamed on Universo Online (UOL), Brazil's largest Internet portal, attracting 1.2 million viewers. The performance was later released on DVD and audiobook formats, and received worldwide attention including reviews by The New York Times and The Guardian. Gentili released a book of the same name [pt] in which he offered humorous criticism of the political times.

The second season of Agora É Tarde was simulcast on BandNews FM. The show expanded to a fourth weeknight as it reached its 100th episode.

In the episode of CQC broadcast on 28 June 2010, Gentili appeared to be assaulted by security guards in São Bernardo do Campo, while recording Proteste Já! about a collapsing school.

In late 2009, Panda Books [pt] published his first book, Como se Tornar o Pior Aluno da Escola [pt] (English: How to become the worst student in school ). The satirical instruction manual soon received a warning label recommending it for those over the age of 18.

Gentili developed a late-night talk show with CQC writer Alex Baldin; a TV pilot was made a condition of his 2009 contract for CQC, and was recorded in 2010. Agora É Tarde (English: It's too late ) premiered in June 2011 on Rede Bandeirantes, with Gentili hosting. It cast Ultraje a Rigor as its supporting band and included comedy routines, stand-up and round-table discussions with other comedians in addition to bringing Brazilian celebrities as the main guests.

He was arrested on 28 October 2009, at Assis, São Paulo, when he recorded a report about the town's zero-tolerance policy against vagrancy while dressed as a homeless man. Danilo was handcuffed and charged with disobedience, public disorder, and contempt.

On 25 July 2009, when trying to interview the president of Brazil's Federal Senate, José Sarney, Gentili was grabbed by one of the president's bodyguards and tossed to the ground. The assault was documented by a photographer from newspaper O Estado de S. Paulo and received national coverage.

Gentili's 2009 book Como se Tornar o Pior Aluno da Escola (English: How to become the worst student in school ) was criticized for being potentially harmful to students. After receiving a warning from the Ministério Público, publisher Panda Books [pt] added a warning seal that it was not suitable for people under 18 years old. This brought more attention to the book and in September 2012 Clube Filmes had reached a deal to make a movie based on it.

Gentili also worked at a cartoonist and caricaturist. In 2008, he collaborated with the Brazilian edition of Mad magazine. During 2008–2009, he wrote a column for Metro Jornal, a popular newspaper in Brazil, and was recognized as "Paulistano of the Year" by Veja magazine.

In 2008, Gentili appeared on the series Custe o Que Custar (CQC, lit. Whatever it Takes), broadcast by Rede Bandeirantes. Gentili initially performed in a segment called the "Reporter Inexperiente" (English: Inexperienced Reporter ) where he asked his guests awkward and unexpected questions with often bizarre turns of events. The segment was an immediate hit and led to a broader take on the same theme where he began to interview people in public, especially about politics.

In April 2008 when he visited the National Congress for the first time, Gentili was expelled for interviewing the president of the Chamber of Deputies, Arlindo Chinaglia, about the tax reform and the usage of tax money by deputies. The report was aired on 24 April.

In 2006, Gentili joined Clube da Comédia Stand-Up [pt] , a stand-up comedy group which performed at local and national festivals. He started a comedy show called Comédia ao Vivo [pt] . Gentili also made small television appearances, mostly on MTV Brasil.

In 2003, Gentili graduated from the Grande ABC University (UniABC) with a degree in social communication (advertising).

Danilo Gentili Jr. (born September 27, 1979) is a Brazilian comedian, television host, writer, cartoonist, and businessman.