In 1995, O'Farrill agreed to direct Chico O'Farrill's Afro Cuban Jazz Orchestra in residence at New York City's Birdland nightclub; the band also performed throughout the world. As a bandleader in his own right, O'Farrill recorded material for Milestone Records, 32 Jazz, and M & I. Those recordings (Blood Lines, A Night in Tunisia, and Cumana) provided listeners with an overview of the musical environment in which O'Farrill was raised. He also made appearances on numerous records, including Habanera with Alberto Shiroma and the soundtrack to the critically acclaimed movie Calle 54.
Arturo was a special guest soloist at three landmark Jazz at Lincoln Center concerts — Afro-Cuban Jazz: Chico O'Farrill's Afro-Cuban Jazz Orchestra, November 1995, Con Alma: The Latin Tinge in Big Band Jazz, September 1998, and the Jazz at Lincoln Center Gala: The Spirit of Tito Puente, November 2001. In March 2002, he was also the featured artist in Jazz at Lincoln Center's Jazz in the Schools Tour, when he led a Latin jazz quintet for 24 educational performances that reached over 5,000 people throughout the N.Y.C. metropolitan schools. He again participated in this educational tour in 2002 and continued to direct the orchestra that preserved much of his father's music.
The year 2008 saw him partnering with vocalist Claudia Acuña for In These Shoes, a stylish offering of jazz and Latin music. Two years later he released The Auction Project, featuring David Bixler, an acoustic post-bop date with a Celtic influence. In February 2011, he followed with 40 Acres and a Burro, an outing for his Afro-Latin Jazz Orchestra. A solo piano date titled The Noguchi Sessions appeared later in 2011; for that album, O'Farrill was recorded alone after-hours at the Noguchi Museum on Long Island.
As a producer, he helmed the sessions for Adam Kromelow's Youngblood album and participated in a quartet known as the Puppeteers with Jaime Affoumado, Bill Ware, and Alex Blake. Their self-titled offering was released in March of 2014. O'Farrill followed it in May with the release of his next Afro-Latin Orchestra date, The Offense of the Drum. The album won a 2015 Grammy Award for Best Latin Jazz Album.
In December of 2014, O’Farrill and his band were in Cuba performing, and planning to record. The next evening, Barack Obama announced the restoration of full diplomatic relations with the nation after more than 50 years of silence. The album O'Farrill had planned was in synchronicity with the announcement: it extended the musical and cultural conversation begun by Dizzy Gillespie and Chano Pozo from the 1940s. It featured four premier Cuban and six American composers/arrangers. The big band was expanded to accommodate 24 players. Its recording sessions included 21 producers and a number of videographers from both countries. The double-length document, entitled Cuba: The Conversation Continues, was released by Motema in the summer of 2015. Two years later, O'Farrill paired with Chucho Valdés for Familia: Tribute to Bebo & Chico, an homage to their legendary fathers and shared musical legacies. ~ Paula Edelstein