[1] While in Jr. high school, he ran away with the Sells & Gray 3-ring tent circus at the age of 15,[2] sleeping in the back of a truck that transported their elephants, Bessie and Anna May.

In 1974, he won a full scholarship to attend the Pennsylvania Governor's School for the Arts at Bucknell University,[4] where he studied theatre under Broadway actress, dancer, and playwright Dr.

[7][8] It opened Off-Broadway on November 15, 1978,[9][10][11] and O'Donnell won three American Society of Composers, Authors, and Publishers (ASCAP) Awards, shared with Dianne Adams (Vocal Arranger, A Gentleman's Guide to Love and Murder).

[12][13] In 1979, for Radio City Music Hall, O'Donnell co-wrote with Scott Bodie Manhattan Showboat produced by Robert Yani, which celebrated over 100 years of American entertainment.

[14] It featured musical direction and arrangements by Tony Award-winning conductor Donald Pippin, and John Corry of The New York Times wrote, "Three Cheers!

[16] In 1983, while living in New York City, O'Donnell was contracted by Tony Award-winning producer James B. McKenzie to create an after-show revue to complement evening performances of the Peninsula Players in Fish Creek, Wisconsin.

[18] While working the Comedy Cabaret, O'Donnell also took to the main stage at Peninsula Players, starring in title roles of Larry Shue's The Nerd and The Foreigner.

[23] Throughout its run, O'Donnell produced, wrote, composed, choreographed, and acted in numerous productions with actors Amy McKenzie, Bobby McGuire, Caroline Schless, Del Close, Lisa Keefe, Megan Cavanagh, Michael Dempsey, Peter Neville, Todd Erickson, and Tom Purcell (executive producer of The Late Show with Stephen Colbert).

[24] It was located at 3207 N. Wilton Ave. Noteworthy productions included O'Donnell's musical comedies An Evening With Elmore & Gwendolyn Putts, The Neighbors Next Door and The TV Dinner Hour (the later featured iO, formerly ImrovOlympic, founder Del Close as The Rev.

"[23] As a stand-up comic, billed as R. O'Donnell, he headlined numerous comedy clubs throughout the 1980s and 90s,[1] including Zanies (where his headshot still hangs on the wall), the Chicago Improv, and Catch A Rising Star, and the Funny Firm where he was a regular headliner and also featured for such national comics as Brian Regan, Rick Overton and Bill Hicks.

[29] He also wrote and directed commercials for McDonald's, Toyota, Jiffy Lube, and Ameritech, starring Besser and stand-up comic Michelle Garb in a stylistic homage to the works of Ernie Kovacs.

In 1999, as R. O'Donnell, he executive produced, wrote, and hosted R. Rated, which aired late night on Fox TV in Chicago.

This comedy variety show included short works by the Annoyance Theatre featuring Rachel Dratch (Saturday Night Live), Mick Napier (The Second City), Tim Kazurinsky (Saturday Night Live), and Stephnie Weir (MADtv), among many other independent film and video makers.

[33][34] For Halloween, October 31, 2008, O'Donnell's Kreep Blog on Static Multimedia and Super Unleaded Design was the cover story for the Chicago Tribune Movies page Screen Scene titled "Kreep-ing Along Poetically".

[34] In 2008, O’Donnell's blog The Kreep received a Coraline handmade box, numbered 46/50, assembled by the stop-motion animation team at Laika films, honoring their favorite bloggers.

This persona, according to Robert K. Elder of the Chicago Tribune, is, “…a Gothic poet and illustrator in the tradition of Edward Gorey.”[34] As B. R. Kreep, O'Donnell has penned numerous poems called Kreeplets[34][37] as well as having written and composed over half a dozen full-scale musical comedies including An Evening With The Kreep, Kreepshow, Kreepmas, Mr. Scrooge, Twist, Kreepy Hollow and Alice Isn't All There.

[40] In 2012, O'Donnell founded the Black Pearl Cabaret with the mission to recruit a professional troupe of actors, variety artists and musicians to perform original works of a Gothic and macabre nature.

[45] Steve Treacy, contributing theatre critic to the Port Townsend Leader, praised O'Donnell's artistry, “His writing, directing, acting and warbling abilities conspire to make him a quadruple threat.

Even his spoken poems, especially “Little Annie Orkle,” are sparkling (no mean feat for that musty old art form).”[45] In a “Best Local Theater of 2013” article published in the PT Leader Arts Section, "Kreepshow," a Gothic comedy cabaret conjuring some spiritual denizens of our Victorian seaport,”[46] was listed as one of the favorite locally written plays penned by Brazillia R. Kreep.

His vision was to create educational, inspirational, and professional opportunities for local artists of all ages while presenting original works based on folklore, literature, and fairy tales.

[59] The title role received a gender twist from Oliver to Olivia, something O'Donnell has established as a sort of signature with his adaptations (see Kreepy Hollow).