His obsessions with Bette Midler led to a gig performing with Midler's back-up girls, The Harlettes. This led to Shaiman and the Harlettes opening for Midler on tour. Knowing her songs and arrangements, he quickly became musical director/arranger for several live shows. In 1980, he became an arranger/composer for Midler's TV movie The Mondo Beyondo Show (1980). One of his big stage credits was for André DeShield's Harlem Nocturne in 1984, as a performer, musical director, orchestrator, arranger and songwriter.
Shaiman's on-screen talents were visible on Saturday Night Live, as a writer and performer (pianist Skip St. Thomas, naturally) for The Sweeney Sisters sketches from 1986-1989. Working with SNL cast member, Billy Crystal, Shaiman wrote the music to Billy Crystal: Don't Get Me Started - The Billy Crystal Special (1986). As an actor, he appeared in Broadcast News (1987) as News Theme Writer. Given his relationship with Midler, he arranged many songs in her film Big Buisness (1988) and Beaches (1988), including favorite "Wind Beneath My Wings".
His collaboration with Crystal lent him to write, adapt, arrange and orchestrate songs for Rob Reiner's film When Harry Met Sally (1989). It wasn't long for Reiner and Shaiman to begin their own collaboration. Their first film together being the decidedly different sounding Misery (1990). He expanded his scoring with Scenes from a Mall (1991), which naturally starred Midler, and also was song and music consultant on her film, For the Boys (1991). That same year he scored the western comedy City Slickers (1991) and the fun lighthearted gothic-gypsy sounds for The Addams Family (1991). Adding to his cameo list, were appearances as piano players in Scenes from a Mall and Hot Shots! (which he didn't score) and as a conductor in Addams Family.
He continued scoring comedies like Sister Act (1992) and Billy Crystal's directorial debut, Mr. Saturday Night (1992), while continuing to write both the score and songs in the films. With Rob Reiner, he scored the courtroom drama A Few Good Men (1992), yet again showing his adaptability in style. With Crystal hosting the 1992 Oscar Ceremony and his penchant for song monologues, Shaiman contributed special musical material, something he would do several times with Crystal. He would win an Emmy for the work. As pianist and arranger, he appeared with Bette Midler on the last episode of The Tonight Show with Johnny Carson in 1992.
1993 brought another popular film, Sleepless in Seattle (1993), which Shaiman wrote the score and song "With a Wink and a Smile" for Harry Connick Jr. The song became Shaiman's first Oscar nomination. And again contributed musical material to that years Oscar ceremony. Following up his films, Shaiman worked on several sequels like Addams Family Values (1993) and City Slickers II: The Legend of Curly's Gold (1994). While not scoring the film, he was a song adaptor and music supervisor for Sister Act 2: Back in the Habit (1993). He also returned with City Slickers director Ron Underwood for his films, Hearts and Souls (1993) and Speechless (1994). He expanded his horizons more with the next Reiner film, North (1994).
Shaiman re-teamed with Crystal, for his next directed film, Forget Paris (1995), and applied a sweeping score to Reiner's next collaboration, The American President (1995). The later received an Oscar nomination - this time for original score. In the next few years, he continued bouncing genres, from comedies like Oscar nominated The First Wives Club (1996), George of the Jungle (1997), In & Out (1997) to Reiner's civil rights drama Ghosts of Mississippi (1997). With Crystal hosting, he again provided material for the Academy Awards in 1997 and 1998. He also score My Giant (1998), another comedy starring Crystal. Like many other composers, Shaiman scored an episode of the miniseries From the Earth to the Moon (1998). Shaiman's style for comedy and drama suited him well for the touching films, Simon Birch (1998) and Patch Adams (1998). The latter became his third Oscar nomination for score.
Working with Trey Parker, Shaiman put on many hats as a composer, orchestrator, arranger, and producer of the album Mr. Hankey's Christmas Classics, and the subsequent South Park episode in 1999. They also worked together on the film, South Park: Bigger, Longer & Uncut (1999). Shaiman composed the incidental score, and co-writing songs with Parker. Their song, "Blame Canada" was nominated for an Oscar - the ceremony in which Matt Stone and Trey Parker arrived in drag, with Shaiman dressed as a pimp.
For Reiner's next film, The Story of Us (1999), Shaiman shared credit with Eric Clapton. He also scored the fantasy comedy The Kid (2000). Returning to TV, Shaiman composed the theme for the series Bette (2000) starring Midler of course, and became the musical director for the Martin Short Show (1999-2000). He also returned with new material for Billy Crystal hosting the Oscars in 2000. He also scored the baseball drama TV movie directed by Crystal, 61* (2001).
2002 became Shaiman's hit year with the opening of his musical Hairpsray on Broadway. Adapted from the 1980s film, and partner/collaborator Scott Whittman, the infectious 60's sound made it a hit and it ran until 2009. The show won the Best Musical Tony award as well as Best Original Score.
Even with his score replaced by David Newman, two original songs by Shaiman/Whittman appear in The Cat in the Hat (2003). His 60s style was used again for the romantic comedy Down with Love (2003), and again scored a Reiner film, the romantic comedy Alex & Emma (2003). In 2004 he wrote material for that year's Oscar ceremony, and collaborated with Trey Parker on songs for Team America: World Police (2004), although his score was rejected after recording the entire thing.
Shaiman returned with Reiner for the romantic comedy Rumor Has It... (2005). In 2006 he returned to the stage with Martin Short: Fame Becomes Me, composing the songs, co-writing lyrics with Scott Whittman, and performing in the show and playing piano.
Continuing with Oscar material, he contributed the song "A Comedian at the Oscars" for the 2007 ceremony. That same year, he scored Reiner's film The Bucket List (2007). It was also the year of the musical film adaptation of Hairspray (2007), arranging and orchestrating the songs from the Broadway hit. With an all-star cast, Shaiman wrote Prop 8: The Musical (2008), a video short that premiered online. For the 2010 Oscars, Shaiman not only wrote special material, but was also the music director. He also scored Reiner's next film, Flipped (2010).
In 2011, Shaiman returned to the 1960s music style with the Broadway show Catch Me If You Can, based on the real case and Spielberg film. Fitting a Broadway composer himself, he wrote the songs for the backstage-musical TV show Smash (2012-2013). He also wrote the underscore for the first 6 episodes. The highlight song "Let Me Be Your Star" was nominated for both a Grammy and Emmy. Continuing his various collaborations, he also scored Reiner's The Magic of Belle Isle (2012) and Parental Guidance (2012) which starred both Bette Midler and Billy Crystal.
Ever the showman, Shaiman has worn several hats throughout his career, appearing in cameos in several films, working for television, stage and screen. He has been able to compose toe-tapping, bouncy scores that hark back to Tin Pan Alley days, and gone to the extreme with endearing dramas. While seemingly type-cast in romantic comedies, he has shown his versatility through the years. His enduring collaborations with actors and Rob Reiner are certainly notable - not to mention the Castle Rock Entertainment jingle that Shaiman wrote. Shaiman continues to expand to different genres, styles and venues - and his wearing of different musical hats makes him a great showman.