In 1990, he graduated from the "Laboratorio di esercitazioni sceniche" (Italian for "Laboratory of scenic exercises"), run by Gigi Proietti in Rome.

One of his most popular roles was Flavio Anceschi, a captain in the Carabinieri, which he played for five seasons in the hit television series Don Matteo on RAI with Terence Hill and Nino Frassica.

The broadcast was highly rated and managed to top the competitor in its time slot Striscia la notizia.

In the same year, he also participated as a dancer for a night in the second episode of the fifth edition of the Rai Uno broadcast Ballando con le Stelle.

In 2011, Insinna hosted the historic broadcast La Corrida (Italian for "The Bullfighting") on Canale 5, personal debut on Mediaset.

Insinna wrote a book, Neanche con un morso all'orecchio (Italian for "Not even with an ear bite"),[2] released on 21 February 2012, which was reprinted four times in a few weeks.

Since 15 September 2012, he hosted the radio broadcast Per favore parlate al conducente (Italian for "Please talk with the driver"), written by Marco Presta and Franco Bertini, aired on Radiodue on Saturdays and Sundays.

In his book Neanche con un morso all'orecchio (Italian for "Not even with an ear bite"), released on 21 February 2012, Insinna blamed the nurse that had prevented him from visiting his dying father during the latter's hospitalisation.

[3][4] In particular, the author included a chapter entitled "L'infermiera stronza" (Italian for "The bitch nurse"), where he wrote: [L'infermiera] guarda e parla con l'inevitabile rabbia che hanno a volte in corpo le donne basse, bruttine e con gli occhiali.

[2](Insinna, Nemmeno con un morso all'orecchio, page 84) Besides, Insinna inserted an unfortunate story about what he would have done to that nurse in the following chapter "Vedrai che andrà tutto bene" (Italian for "It'll be fine"): [L'infermiera] arriva alla sua auto, apre lo sportello e non fa in tempo a salire, arrivo da dietro, la prendo per il collo e le sbatto la faccia contro la sua automobilina nuova nuova, comprata in sedici comode rate.

Ce l'hai o ti hanno creato in laboratorio alla fine di un esperimento poco riuscito?

(...) E se provi a denunciarmi io domani torno e ti ammazzo con le mie mani.

[3][4][7] Later in 2017, Striscia la notizia broadcast a TV report about this topic, underlining the violent and misogynistic tone Insinna used in his book, worsened by the fact that the author had certainly pondered those words, talking about "bullying, a violence against women that goes so far as to femicide".

[7] In 2017 Striscia la notizia broadcast a TV report aimed at exposing Insinna's duplicity, showing the host talking off the air while recording some episodes of Affari tuoi.

In a leaked tape of 25 September 2014, a fuming Insinna scurrilously complained about the "box X", a special option of the game, which he considered completely useless.

Fidatevi, senti uno stronzo una volta, la "X" non ci fa vincere le serate!

Con questa rottura di cazzo, la regola, trentasette puntate, ma prendiamo cinque stronzi fatti bene!

Una nana che parla con le mani davanti alla bocca, se no sta muta.

"Er concorrente, no, non te li famo vede', scegliamo noi", ma che cazzo scegliete?

Per quelle di mezz'ora famo i salti mortali, poi per quella de tre ore 'amo portato i figli del dio minore!

[20][21][22][23] The lawyers Fausto Gianelli and Dario Rossi sued RAI on behalf of Associazione Palestinesi in Italia (Association of Palestinians in Italy) and Associazione benefica di solidarietà con il popolo Palestinese (Charity association for solidarity with Palestinian people).

[20][22][23] Considering that "it's common knowledge that on 21 December 2017 Italy voted in favour of the United Nations' resolution refusing USA's decision to recognise Jerusalem as the capital of Israel, as well as United Nations themselves repeatedly blamed Israeli occupation of Palestinian territory and East Jerusalem, denying the validity of Israel's decision to turn Jerusalem into their capital", being United Nations' decision directly applicable to Italian legislation, the Court of Rome, Person and Immigration Rights Section, completely agreed with the petitioners with its decision dated 3 August 2020 and registered as RG 31253/2020, forcing RAI to read the following statement during the next episode of L'eredità: "International law doesn't recognise Jerusalem as the capital of the State of Israel".

The Court of Rome, Eighteenth Civil Section, eventually decided that Insinna's rectification of 6 June 2020 was to be considered enough without further clarification with its decision dated 20 October 2020 and registered as RG 40043/2020.

[25] During the Christmas 2020 episode of L'eredità, Insinna read the following question: "In 1869, which sentence did Cavour pronounce to inform the Piedmont ambassador that Garibaldi had entered Neaples?"

Many people, including Mario Adinolfi, noticed that the question contained a huge mistake, reacting ironically and polemically.

Subsequently, Federcaccia (the Italian Federation of Hunting) reacted by writing a letter of complaint signed by its Director Massimo Buconi to RAI and to the related Parliament Commission, at the same time threatening to sue Insinna for defamation and inviting the audience to stop watching the TV broadcast.

Fratelli d'Italia senator Giovanbattista Fazzolari said: "The overpaid (with public money) TV host Flavio Insinna states he's contrary to military expenditure.