Grimaldi was born in Melrose Park, Illinois. He is a graduate of Proviso East High School. He studied dance at the Stone-Camryn School and Gail Larry School, Ronn Forella, Luigi and with John Aristides, and Jack Cole. Under the tutelage of Eugenie Leontovich, Dr. John Reich, and Dr. Charles McGaw, he graduated with a Bachelor of Fine Arts in acting on scholarship from Goodman School of Drama at the Art Institute of Chicago, and also studied at Indiana University. As an actor and dancer, he co-starred in A Flea in Her Ear, Caesar and Cleopatra, The Sound of Music, Funny Girl, A Song for Cyrano, and Follies. As a dancer, he also appeared in Man of La Mancha, Hello, Dolly!, Promises, Promises, Sugar and other productions.
Career
After his career as a dancer and actor, Grimaldi began directing and choreographing. In 1989, he formed Dennis Grimaldi Productions. For the stage, he first worked as an Associate to the Producers on A. R. Gurney's Sweet Sue. He recently Directed Alfo Learns to Love and produced and directed the Workshop Production of Harry Townsend's Last Stand starring Len Cariou by George Eastman. His many credits as Producer include The New Ork City Center Production of Harry Townsend’s Last Stand starring Tony Award winner, Len Cariou and Craig Bierko, Executive Producer for the television film of the Sondheim/Laurents/Styne Musical Gypsy which was filmed live at the Savoy Theatre in London and starred Olivier-winner Imelda Staunton, As a producer for Broadway, productions include The Heidi Chronicles with Elisabeth Moss, Jason Biggs and Bryce Pinkham, the Bernstein/Comden/Green musical On the Town 2014 revival, and The Realistic Joneses starring Toni Collette, Michael C. Hall, Tracy Letts and Marisa Tomei. In 2014 he won the Grand Slam of theater awards, the Tony, Drama Desk, Drama League and Outer Critics Circle Awards for "Best Musical" for the Broadway production of A Gentleman's Guide To Love and Murder starring Tony winner Jefferson Mays. Grimaldi's other Broadway productions include the Deaf West Broadway revival production of Spring Awakening; Love Letters, the musical revival of On the Town, and the Australian tour of Driving Miss Daisy. He is co-producer of the Tony-winning George and Ira Gershwin musical, Nice Work If You Can Get It. The musical received 10 Tony nominations, 9 Drama Desk nominations and 9 Outer Critics Circle nominations. For the 2011 season, Grimaldi was involved with the highly successful musical production tour of A Christmas Story; it was nominated for a Tony Award as Best Musical In the fall of 2012. He was to co-produce the musical Rebecca based on the Daphne du Maurier novel, directed by Tony Award-winning Michael Blakemore, but the production was stalled due to the collapse of a Ponzi scheme which collected thousands of dollars from the production. The team, Mark and Sherri Hotton, were arrested and charged with wire fraud, awaiting sentencing as of November 2012. Other productions on Broadway and Off-Broadway included the 2011 Broadway revival of the Stephen Schwartz musical Godspell; Leslie Jordon's My Trip Down The Pink Carpet; also Angels in America,Other People's Money, the Olivier Award-winning Rise and Fall of Little Voice,Girl's Room,Sally Marr, Grace & Glorie,Artist Descending a Staircase,The High Rollers, The Boys in the Band revival, Any Given Day, and Party. He was also involved with the musicals Nunsense Jamboree, Fanny Hill and Annie Warbucks , which had the distinction to also perform for the White House, Like Love, and the musical adaptation of A.R. Gurney's Richard Cory, among others. He has also been associated with Emanuel Azenberg on the Neil Simon productions of Lost in Yonkers and London Suite as well as the Broadway production Chita Rivera: The Dancer's Life with The Producer Circle and David Mamet's The Cryptogram and, in 2015, the Broadway production of Terrence McNally's It's Only a Play starring Nathan Lane, Matthew Broderick, Megan Mullally, Stockard Channing, Rupert Grint and F. Murray Abraham. His many London productions on the West End and The Fringe include The Boys in the Band, Stephen Sondheim's Marry Me A Little, actor Jack Gilford in Look To the Rainbow and John Lahr's Diary of a Somebody. He produced the Martin Charnin revue Something Funny's Going On. He was an associate on the Off-Broadway production of Oblivion Postponed by Ron Newseyer, directed by Nicholas Martin. He was an associate producer for Candid Productions, a television production company, for 15 years; producing programming for ABC, NBC and HBO. He was awarded the Robert Whitehead Award for Excellence in Theatre Production, the NY Film and Television Gold Medal Awards, the Outer Critics Awards and the Carbonell Award. Productions have also earned The Drama Desk, Drama League and Tony Awards, as well as the Pulitzer Prize. Mr. Grimaldi in New York, recently directed Stephan DeGhelder's Looking For Mr. Right and Vincent Amelio's Romantic Italian Comedy, Alfo Learns to Love.