Self-taught, Leo began drawing at the early age of five, when he was commissioned to do his first portrait. Working in the mediums of pencil, pastel, acrylics, watercolor, and oils his artwork is characterized by the photo-realism that captures the heartbeat of his subjects. A graduate of East Forsyth High School, he received a scholastic gold key and a merit award for art during his senior year in 1981. After applying for summer work through the R.J. Reynolds summer program, he attended Rutledge College, where he received a commercial art degree and an outstanding artist award in 1983.

At the beginning, in his first employment, his employer noticed his artistic talent and sent him to Charlottesville, Virginia to train and learn the gold leaf technique in the framing business. In 1990, he received a merit award for his pencil drawings. In 1991 he received first place for his pencil drawing called "Portrait of Parenthood" as well as in 1992 for his oil painting "Baby Brown Eyes."

By 1993, he was selected as the featured artist by the African Americans' Arts Festival advisory committee for its annual festival. His pastel painting "Young Dreamer" was used as the cover for that year's brochure and poster. This allowed Leo to have his first one man exhibit at the African American Atelier Gallery in Greensboro, North Carolina.

In 1994, he began an ongoing relationship with McCleansville Middle School in McCleansville, North Carolina to do Artist and Career Day demonstrations. In 1995, Leo was commissioned by Jefferson Diggs Elementary to paint a mural in their entrance area about the school's Arts and Academics program. In 1996 he worked with Forsyth Early Childhood Partnerships, one of Governor Jim Hunt's programs and at Smart Start, where he created images for its Keepsake Book, a helpful guide for mothers caring for their babies after delivery.

Leo also created paintings and drawings that were used for annual report covers, posters, billboards, and newspaper ads. In the same year, he is currently commissioned by SMSI Marketing to render pastel portraits of successful ethnic women. These portraits are used in Sophisticate Black Hair Magazine under its "Role Models Beyond Beauty" section, which has become one of the largest collection images to date done by the artist, a count of 136 to date.

In 1997, Leo was the winner of the Stokes County Arts Council Landmark Print Competition. A signed and numbered print was developed to raise money to enable the continuation of community and in-school arts programming. In 1998, he designed a logo and a flip chart for Baptist Hospital's Outreach Screening and Education Project in Mammography for Women.

Leo has also helped to design logos for the Greater Cleveland Avenue Christian Church clothing line called Wear Christ Only gear. In addition to this, he also created and painted the borders in the children's church rooms within the new building.

In 1999, Leo was featured in Art Business News and Shades of Beauty Magazine. During this time, he also began working with the 1999 and 2001 Winston-Salem Arts Council summer program "Artiva," and he began teaching a figure drawing class for the summer honors arts students. In 2000, he designed a poster for the 40th Anniversary of Neighborhood Bible Studies, Inc. out of Dobbs Ferry, New York.

As an illustrator for Cultural Hang-ups, Mr. Rucker did the first four images for multicultural borders and wall covering . 2001- 2002 commissioned by the Winston-Salem Rehab Center to paint a mural in its entrance area, along with creating a poster for Vision Works, Inc. a program for at risk youth who may have trouble staying in school. Also, he was an art teacher for The Artistic Studio in Winston-Salem, North Carolina, for Pre-K and first grade classes.

2002 commission by Carlton and Helen Rucker to paint a Winnie the Pooh mural in baby room, also commissioned by Truilant Credit Union to paint five portraits and by Allegacy Credit Union to draw its board members.  In 2003 a one -man exhibition at the Delta Fine Arts Gallery in Winston Salem, NC, taught an after art class at Lathan Elementary in Winston Salem and commissioned by the Winston Lake YMCA to paint a mural of it’s history contribution to the community where it is located as well as commissioned by the North Carolina board of attorney to paint a portrait of Judge Roland Hayes the first elected Africa American in Winston Salem Court system. 2004 commission by Flavored Foods a Keller Texas company to create an image for its marinades and sauces label, 2003-2004 commissioned by Rubin McClain of Reynolds Home Care a Winston-Salem based company to paint his first Trompe’lo mural in his office, Poetry and Art exhibit with poet Linda Hollingsworth in the Melton Rose gallery /Sawtooth Building. 2005 contracted by the Danville Virginia AAF Tank Museum to create and paint varies murals, and by the Winston Salem State University Friends of the Library to paint a 20th year anniversary history piece. Also commissioned by Winston Salem Susan Komer Cancer Society and worked with Lowrance Middle School physically challenge students in art.