It wasn't long after that Woo got her start in show business as a Las Vegas show girl in Marshall Edson's review, Holiday in the Orient. The headliner of that show was the late Sammy Tong, who is best remembered as "Charlie" in the Bachelor Father television series. Later, Woo was selected, from many hopefuls, to open the Hollywood Playboy Club as one of the original Playboy Bunnies.
Even though Woo thoroughly enjoyed her time with the Hollywood Playboy Club she was soon offered an opportunity to pursue a singing career with popular entertainer "Mr. Bongo," Jack Costanzo. Jack, who at one time performed with the likes of Stan Kenton, Judy Garland and Nat "King" Cole, introduced the conga drum to jazz and rock music. Woo's first singing engagement with Costanzo was at the Sands Hotel in Las Vegas. With her combination of talent and verve, it was apparent right from the start that Woo was the perfect addition to the Costanzo group. Costanzo and Woo earned raved reviews from the critics in Las Vegas particularly after they introduced a new, fast-rising Latin number "La Bamba" to the Tropicana.
Upon completion of their engagement in Las Vegas, Costanzo and Woo headed for Puerto Rico. What was originally thought to be a short booking engagement at the El San Juan Hotel turned out to be one of the Hotel's longest gigs, a contract for the entire season! While at the El San Juan, Tico Label signed Woo to do an album with Jack Costanzo called Latin Percussion with Soul. Other albums followed, notably their most popular album, Viva Tirado on the Crescendo Label.
The group went on to entertain the American GIs at USO shows in Vietnam, the Philippines and Bangkok. Woo would later reflect, "My greatest experience was when we toured the Far East, especially when we penetrated deep into enemy territory in Vietnam to entertain the troops. What thrilled me years later was when someone in the audience would walk up to the bandstand and say, 'I first saw you and Jack Costanzo in Nam and here I am seeing you again in the USA!'"
For over 25 years, Costanzo and Woo continued to entertain around the world in their unique and dynamic style with a mixture of Latin music, R&B, jazz, rock and classic ballads; they became particular favorites in San Diego at such notable clubs as the Stardust Hotel and Country Club, the Catamaran, the Hotel Del Coronado and the Copacabana Restaurant. For several of those years Jack was not only the band leader, he was also Woo's husband. Even after they were no longer Mr. and Mrs. Costanzo, they continued to perform together for many years.
Woo, who also fronted other groups such as Pitch and Woo and Woo's Folly admitted that the performing chemistry between her and Jack was special. "We just work well together," said Woo. "We worked with other people, but it's not the same."