Beginning at historic St. Francis Chapel in December 1988, the Keelans and their talented friends have entertained thousands. Originally called "WinterFest" the first three years, it featured carols and solos of the holiday season, an abridged "Messiah" performance and other classical music offerings. It was renamed in 1991 as Keelan & Friends holiday carol music events and became a community tradition at St. Francis Chapel. When the chapel was sold to the Catholic church in 1998, the Keelan concerts then moved to various major church sanctuaries each Christmas since 1999, including St. Paul United Methodist; First Presbyterian, Trinity United Methodist; First Plymouth United Church of Christ and Rosemont Alliance Christian Church. The concerts originated as fundraisers for the St. Francis Chapel, but since have raised funds and awareness for a wide variety of charitable causes including People's City Mission; Lincoln Food Bank; Make-A-Wish Foundation; Voices of Hope; Fresh Start; CASA (Court-Appointed Special Attornies); Catholic Social Services; Mourning Hope; Friendship Home; Northeast Family Center; Salvation Army, Matt Talbot Kitchen, Autism Family Network; Heartland Myasthenia Gravis Foundation and others. All monies gathered in ticket sales go to the chosen organization.

In 1998 Malley and friends presented their first Mother's Day Bouquet of Song concert. The first HymnFest was held in 2005 and other theme concerts were presented over the last two decades at St. Francis Chapel, First Presbyterian, Vine UCC., Southminster UMC and First UMC. These included the popular Keelan Irish music shows and several Gilbert & Sullivan musical events, as well as classical chamber music concerts.

Since 2003 the Advertising Federation of Lincon has been the "flagship" sponsor of the Keelan Family & Friends Christmas concerts.  Various Lincoln businesses such as Butherus, Maser & Love Funeral Home; Roper & Sons Funeral Services; Peoples Choice Federal Credit Union and Hanna-Keelan Planning as well as "in-kind" help by Augstum's Printing have also generously contributed financially to enable these events to continue.

The Keelans have been blessed to be associated with many of the finest musical artists in the Lincoln-Omaha area: trumpeter Mac McCune; organists John Cummins, Nic Engel and Murray Foreman; pianists Wilma Sundeen, David Abbott, Audun Ravnan, Joan Allen; flutist Betsy Bobenhouse; cellist Kim Cook as well as many professional singers in this area. Noted literature, theater and media personalities Ted Kooser; Roy Scheele; Bill Kloefkorn; Lora Black; Pippa White; Leta Powell Drake; the late Rev. Dale Holt, John Cutler, and Cathy Blythe & Scott Young among others have made each event memorable with special readings.