Shankman moved back to Los Angeles and started dancing in music videos. He was a Dancer in Janet Jackson's "Alright" video, as well as in an MC Skat Kat video with Paula Abdul. Shankman broke into professional choreography in a 1989 music video for Rapper MC Shan with Director Julien Temple. When the hired Choreographer fell through, Shankman lied and said that he had done choreography for Janet Jackson and Paula Abdul. He was hired on the spot without his story being verified. As a Choreographer, he worked with acts including Tony! Toni! Toné!, The Time, Whitney Houston, and Aaron Neville. In 1996 he won a Bob Fosse Award for Best Choreography In a Commercial. On television, he was a go-to Choreographer on Friends and The Ellen DeGeneres Show. He served as a Choreographer and dance consultant on dozens of movies including Addams Family Values, Catch Me If You Can, George of the Jungle and Boogie Nights.

Shankman danced on the Oscars telecast in 1990, and exactly 20 years later was Producer and Choreographer on the 82nd Oscars. At the 1990 Oscars, Shankman danced in the number "Under the Sea", where he met his best friend (a Dancer in the same number), Director and Choreographer Anne Fletcher.

In 1998 Shankman wrote and directed Cosmo's Tale, a non-dialogue short film that appeared at the Sundance Film Festival. Following the short, his sister, Jennifer Gibgot, asked him to read a script that she had already set up with Fine Line Features, entitled The Wedding Planner. He liked the script and this led to a meeting with execs. He was hired for the job of Director ten minutes into the meeting. The movie eventually went to Columbia Pictures and was a box office success.

Following The Wedding Planner, Shankman went on to direct seven more studio films: A Walk to Remember, Cheaper by the Dozen 2, Bringing Down the House The Pacifier, the 2007 award-winning film Hairspray, Walt Disney Studios Motion Pictures' Bedtime Stories, and the movie based on the musical of the same name, Rock of Ages.

Shankman serves on the board of The Trevor Project and co-founded the DizzyFeet Foundation with his friend Nigel Lythgoe. This was founded in 2009 to support, improve, and increase access to dance education in the United States by providing grants to after school dance and arts programs in low income areas and rewarding scholarships to talented Dancers across the country. The foundation is the biggest supporter and trailblazer for National Dance Day, hosting various events every July across the United States.

With Bill Mechanic, Shankman was one of the two producers of the 82nd Academy Awards, which took place on March 7, 2010. The telecast earned a record 12 Primetime Emmy Award nominations, including two for Shankman, for Best Choreography and Co-Producing.

In 2012, Shankman directed a dual campaign to attract young voters for Rock the Vote and Funny or Die. In June 2017, he directed the pilot for Step Up: High Water, a new television series produced by Lionsgate Television and Youtube Red.

In August 2014, Shankman directed and choreographed a production of Hair at the Hollywood Bowl. Zach Woodlee assisted Shankman in choreography and Lon Hoyt served as music Director. The show presented an all-star cast including Benjamin Walker as Berger, Kristen Bell as Sheila and Hunter Parrish as Claude. Other cast members included Sarah Hyland, Jenna Ushkowitz, Mario, Kevin Chamberlin, Beverly D'Angelo and Amber Riley. As is customary with the annual Bowl musicals, the Hair cast had fewer than 14 days to get the semi-staged show up and running. Shankman and his team had the task of teaching dialogue, choreography, music and lyrics for over forty numbers to a cast of thirty, in just ten days before going on to dress rehearsals. The cast and crew had only two dress rehearsals before going live to a crowd of 11,000 people. The show garnered positive reviews, including one from BroadwayWorld.com: "Overall, Shankman's production of HAIR for the Hollywood Bowl is definitely a must-see event this weekend. Steeped in dazzling visuals, fun music, high-energy choreography, and a cast of talented, staggeringly gorgeous youngsters with giddiness coming out of every pore, this musical celebration of peace, love, and happiness deserves your attention."

In 2015, Warner Bros. Theater Ventures started developing a musical version of the 2009 movie 17 Again, which was directed by Burr Steers and produced by Shankman and Gibgot. The show was workshopped in New York's theater district, with a run planned for the near Future. The musical is being produced by Warner Bros. Theater Ventures, Mark Kaufman and Adam Shankman.