After growing up in Cleveland, Ryan is well known for singing about the
American West. In summer 1966, Will's earlier band, Wead, played a gig in Wellington, Ohio. Appearing on the same bill was Akron-based girl-group The Poor Girls, featuring 17-year-old Chrissie Hynde.
In late 1970s he teamed up with Phil Baron as Willio and Phillio. They had regular gigs on television, radio and comedy clubs and universities throughout the U.S.. They later paired up again voicing characters of best friends Teddy Ruxpin (Baron) and Grubby the Octopede (Ryan) in the Teddy Ruxpin book and tape series as well as the 1987 television show The Adventures of Teddy Ruxpin. In August 2002, Willio and Phillio returned to Cleveland for two performances, at historic Cain Park and two days later at the famed Beachland Ballroom. At the Cain Park show, friend Alec Nordstrom of Hudson was invited onstage. Cleveland's revered rock critic and "world's oldest teenager," Jane Scott, attended and reviewed the Beachland performance for the Cleveland Plain Dealer. The Willio and Phillio act brought Ryan back into music and after moving to California, he began to write and record songs for The Walt Disney Company.
Willio and Phillio performed "I Wish it Could Be Christmas All Year Long" on a Disney Christmas album in a voice similar to Micky Dolenz of The Monkees.
He provided the voices of Rabbit and Tigger, and the singing voice of Eeyore in the Disney Channel's long-running series Welcome to Pooh Corner and in many other Pooh cartoons. He also provided the voice of Barnaby the Dog on the popular series Dumbo's Circus.
In 1987, Ryan became a fixture of the radio drama Adventures in Odyssey, as Eugene Meltsner, Harlow Doyle, David Harley, Patrick O'Ryan and nearly 100 one-shot characters. He voiced Rabbit in Winnie the Pooh and a Day for Eeyore, Digit in An American Tail, Petrie in The Land Before Time, and Willie the Giant in Mickey's Christmas Carol He continues to do voice work. In 2009, he was working on the third season of Mickey Mouse Clubhouse, the 21st season of Adventures in Odyssey, and the new radio series of Will Ryan's Cactus County Round-Up. In the Family Guy episode "Road to the North Pole", he provided the voice for Winnie-the-Pooh. As a side project, with Andrew J. Lederer and Michael Rosenberg (Jackie Diamond),
Will Ryan briefly performed in the '20s-style music and comedy trio, The Merry Metronomes. He and Lederer also appeared from time to time as a duo, usually under the name The Natty Nabobs. He and Nick Santa Maria also perform occasionally as a vaudeville-era comedy team, Biffle & Shooster (Ryan plays the latter), and in 2013 they made their first film, a faux 1930s comedy short titled It's a Frame-Up!.