Has to be done with the flying shot. Daredevil icons are awarded for flying close to the ground or a tower (flying under bridges works also). This can be unlocked on any level with the flying shot but will probably take some practice.
Alternate Method: You want to start off with a low powered shot to the left. This should cause the Flying Shot to barely miss the cliff and as soon as you activate you should receive #1 (indicated by the blue icon). The red line is the path that I took. You want to barely miss the column to get the icon. Once you get to the last gray pillar, you want to start dive bombing the ground then raising back up. You also have an opportunity to get a daredevil on the last round pillar that you are normally supposed to destroy. I found it A LOT easier to weave left and right through the pillars then to try and weave up and down with the arches/pillars. Hopefully this isn't too confusing.
DEG23 Credits: Thee Elf for the Alternate Method and Image provided.