Shaiman started his career as a theatre/cabaret musical director. He then became vocal arranger for Bette Midler, eventually becoming her musical director and co-producer of many of her recordings, including The Wind Beneath My Wings and From a Distance. He helped create the material for her Emmy Award winning performance on the penultimate Tonight Show with Johnny Carson. His work with both Bette Midler and Billy Crystal led to his involvement on their films.
Shaiman has earned five Academy Award nominations, a Tony Award and a Grammy Award for his work on the musicalHairspray, and an Emmy Award for co-writing Billy Crystal's Academy Award performances. He has also been Grammy nominated twice for his arrangements for Harry Connick Jr.'s recordings When Harry Met Sally... and We Are in Love and Emmy nominated for his work on Saturday Night Live. In 2002, he was honored with the "Outstanding Achievement in Music-In-Film" award at The Hollywood Film Festival, and in 2007 he was honored with ASCAP's Henry Mancini Award in recognition of his outstanding achievements and contributions to the music of film and television. He is the first recipent of the Film & TV Music Award for Best Score for a Comedy Feature Film.