Roberto Bolle trained at the School of La Scala Theatre in Milan, where he has been Étoile since 2004. He has danced in all the major theaters around the world and with the most prestigious companies, including the American Ballet Theatre, the Opera National de Paris, the Bolshoi Ballet, the Mariinsky - Kirov Ballet and the Royal Ballet.

In June 2002 he performed at the Golden Jubilee of Queen Elizabeth at Buckingham Palace. The event was broadcast worldwide by the BBC.

In April 2004 he danced in front of Pope John Paul II in the churchyard of St. Peter's Square in Rome for World Youth Day.

In February 2006 he performed in the opening ceremony of the Winter Olympics in Turin, broadcast around the world.

Starting in 2008 he has had enormous success with the Gala “Roberto Bolle and Friends” in places never before reached by any dancer: the churchyard of Milan Cathedral and Piazza Plebiscito in Naples, where he has been followed by thousands of people. He has performed exceptional shows in the magical setting of the Colosseum and the Baths of Caracalla in Rome, in the Temples Valley in Agrigento, at the Certosa of Capri, in the Boboli Gardens in Florence, at Torre del Lago Puccini and in Piazza San Marco in Venice.

After the resounding success and critical acclaim of his debut at the Metropolitan Opera House in New York in 2007, where he danced with Alessandra Ferri for her farewell to the stage, he was appointed " Principal Dancer" of the American Ballet Theatre in 2009, honor never before bestowed on an Italian dancer. Every year since then, he has been one of the protagonists of the ABT season.

In 2013, the “Roberto Bolle and Friends” Gala was inserted in the project, sponsored by the Italian Ministry of Foreign Affairs, "2013, Year of Italian Culture in the United States" performed at the New York City Center in New York.

Since 1999, he has served as Goodwill Ambassador for UNICEF, participating in a series of large and significant initiatives, including trips made in 2006 to the South of Sudan and in November 2010 to the Central African Republic, to bring direct evidence of the tragic situation of the people of those countries.

In 2009 he was appointed a “Youg Global Leader” by the World Economic Forum of Davos.

In 2010 he met two great directors: Peter Greenaway, who asked him to interpret the symbol of Italian art in his installation "Italy of cities" - designed for the Italian pavilion at Expo Shanghai 2010 - and Robert Wilson, who devoted to him one of his voom portrait, "Perchance to Dream" in an impressive multimedia installation, inaugurated in New York in November.

In 2012 the prestigious title of "Knight of the Order of Merit of the Italian Republic" was bestowed upon him by the President of the Republic, Giorgio Napolitano, because of merit acquired to the country in the cultural field.

In 2014 he was awarded the UNESCO Gold Medal, conferred in Paris, for the universal cultural value of his artistic work “reward of his contribution to the promotion of the ideas of UNESCO through dance as a living cultural expression and vector for dialogue”.

In 2014 Bolle was chosen as the star of the new ENI campaign "Rethink Energy" for which he made a spot directed by Fabrizio Ferri. The relationship with the energy company ENI supports the Étoile in a series of artistic and cultural initiatives in Italy and abroad.

In April of 2015 Rizzoli released the book "Voyage into Beauty" with beautiful pictures that portray him with some of the symbols of the Italian artistic heritage. In particular the photos by Fabrizio Ferri depict the statuesque dancer in the ruins of Pompei, in the frame of Roman frescoes, a symbol of the greatness of Italian history and the need to preserve its memory. In photos by Luciano Romano, in Piazza San Marco in Agrigento, from the Colosseum to the Baths of Caracalla, the harmony of gestures and the balance between the dancer and the places evoke a profound reflection on “art and the exceptional nature of Italian heritage”.

In 2015 Roberto Bolle approached for the first time in the role of cinema director participating in the choral project "Milan 2015" documentary film produced by Lumière & Co. of Lionello Cerri, on the subject of Christian Mainardi and divided into six episodes with as many directors: Roberto Bolle, Walter Veltroni, Silvio Soldini, Giorgio Dritti, Elio of “Elio e Le Storie Tese” and Cristiana Capotondi. The film, successfully presented at the Venice Film Festival, has been released in theaters in October 2015 and in videos seen on Sky and RAI Cinema.

In 2016 he guested at the very popular Sanremo Italian Song Festival, performing a new choreography by Mauro Bigonzetti on We Will Rock You by The Queen.

In October 2016 Raiuno, the main Italian tv channel, devoted him a prime time Saturday evening with the show event “Roberto Bolle – La mia Danza Libera” and in November Italian cinemas have released “Roberto Bolle – L’arte della danza”, a documentary film adapted from 2015 summer tour “Roberto Bolle and Friends”.

The 1st January 2018 was broadcasted, again on Raiuno, a new tv event of great dance: "Roberto Bolle – Danza con me". On January he also performed in “The Seasons” a world premiere ballet performance opening the World Economic Forum Annual Meeting 2018 in Davos (Switzerland).

In September 2018 he received the Honor of "Officer of the Order of Merit of the Italian Republic".

In June 2018, he was the Artstic Director and performer of the first edition of “OnDance | Accendiamo la danza”, the great feast of all dances that took place in Milan and that in 2019 returned with the second edition in Milan and, for the first time, in Naples.

The beginning of 2019 saw him once again starring in the tv show on Rai1 "Danza con me", acclaimed by critics and the public, also the 2020 and 2021 editions were very successful. In March 2019 the TV documentary, he himself created, "This night has opened my eyes" was broadcast on Sky Arte.

“OnDance | Accendiamo la danza” had its third edition in Milan in 2020, both in presence and streaming. A great challenge due to the health emergency, but an important signal of the desire to return to dance and share with the public.

In 2021 he created the multimedia project OnDance - Le Masterclass in collaboration with Tim Vision with a rich program of ballet and other styles classes.

In May 2021, he was awarded the title of Grand Officer of the Order of Merit of the Italian Republic by the President of the Republic Sergio Mattarella.