Born and raised in Baton Rouge, Louisiana, Philip was hired - soon after college - as a vocalist with Ray Conniff and his Orchestra; he spent the next three years touring internationally. Upon his return to the U.S., he moved to New York, where he has appeared in concerts (including Encores! at City Center and Lyrics and Lyricists at the 92nd Street Y) and in theatrical evenings, including the Broadway premiere of Alan Menken and Tim Rice's King David. He's featured on a number of studio cast recordings - among them, the Gershwins' Sweet Little Devil and Pardon My English, Kitty's Kisses and Sweet Bye and Bye, plus the highly acclaimed Maury Yeston Songbook. He performs regularly in and around New York, where favorite roles include Gabey in On the Town, Joe Hardy in Damn Yankees, Spike in Song of Singapore, and Curly in Oklahoma! He recently completed a run as Arnold in the Off-Broadway revival of The Boys Next Door.

His debut album, Where Do I Go From You?, featuring songs and arrangements of the big-band era, came out in November of 2000; Show Business called it "lush and lavish, a tenor's dream... Chaffin has a flexible and soaring instrument whose honey-colored timbre is both refreshing and sexy." His second album, Warm Spring Night, took on seventy years of romantic Broadway song. National Public Radio raved, "If you have a love for passion and romance as expressed in great musical theatre songs, you should do yourself a favor and seek out Warm Spring Night, a wonderful collection of romantic musical numbers." His third solo disc, When the Wind Blows South, allowed him to revisit his Southern roots and bring them to bear on the music he loves best.

His fourth solo disc, Somethin' Real Special (The Songs of Dorothy Fields) was released in November 2013. It graced several "year's best" lists and prompted write-ups in The Huffington Post and USA Today; the venerable entertainment magazine Show Business cheered, "Chaffin’s gorgeous, soaring baritone will make you hear these old songs in a fresh and thrilling new way."

Where Do I Go From You? launched the record label PS Classics, for which Philip serves as A&R Director. These days, Philip divides his time between performing and running PS Classics, which is dedicated to the heritage of Broadway and American Popular Song. As A&R Director, Philip reviews all submissions and ultimately greenlights all recordings - in particular, those involving the vocal artists who'll appear on solo albums and compilations. Solo artists on the PS Classics roster include Maureen McGovern, Liz Callaway, Christine Andreas, Rebecca Luker, Steven Pasquale, Jessica Molaskey and Victoria Clark; its cast albums - including Sondheim on Sondheim, A Little Night Music, Nine: The Musical, Assassins, Grey Gardens and Company - have been honored with eight Grammy nominations. Recently, Philip has been taking a more active role in album producing; in 2011, 2013 and 2015, he received Grammy nominations for producing the Broadway Cast Recordings of Sondheim on Sondheim, Follies, and Fun Home.