Winnie Winkle
In the 1980s and 1990s, Bolle drew and lettered the Sunday and daily Tribune Media Services strip "Winnie Winkle", either from 1982–1996 or, he has said, "for 20 years". He performed those same functions on King Features' "The Heart of Juliet Jones" from 1989–2000, either for both dailies and Sundays or "just dailies". He lettered Tribune's venerable "Annie" daily and Sunday strips in the 1980s through 1999, contributing, as well, a small amount of art as a ghost artist. Finally, he did ghost art on Tribune Media's "Gil Thorp" in 1995, 1996 and 2008. Credited, he drew the daily and Sunday North America Syndicate strip "Apartment 3-G" in 1999. He continued with the strip through its finale in November 2015, by which point Bolle was 91.