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In 1999 Watkins joined Maynard Ferguson as Trombonist, Musical Director, and Arranger for the legendary jazz trumpet player. On the road with Ferguson, he performed thousands of gigs and educational workshops worldwide. He can be found on many audio and video releases with Ferguson and his band. Reggie is featured Trombonist and Arranger on the 2001 Maynard Ferguson/Diane Schuur release 'Swingin For Schuur'.

In 2003 Reggie was selected as one of only eleven semi-finalists to perform at the prestigious 2003 Thelonious Monk Institute International Jazz Competition in Washington D.C.

In 2004 Watkins released his first solo CD as Band Leader, Trombonist, Composer, Arranger, and Producer entitled A-LIST. The album features sixteen musicians, all original compositions and arrangements, and is part of "The Maynard Ferguson Presents Series".

In 2008 he joined the Grooveline Horns and began touring with Jason Mraz. In 2009 the group performed on "Saturday Night Live", "The Today Show", at Radio City Music Hall, The Royal Albert Hall, The Hollywood Bowl, The Java Jazz Festival, The Oxygen Festival, Farm Aid, "The Tonight Show with Conan O'brien" and an extensive world tour.