I may be wrong but I think a compound flower would be the hardest to pollinate as each individual small flower would have to be dabbed.They open at different times starting in the middle and working progressively outward.
They would have to be covered to prohibit insect pollination.I suggest daylilies as results are more satisfactory.For vegatables I suggest squash or pumpkins.
Charlie

Hi! I am a grad student at the U of MN and asked another student who is actually making crosses between sunflowers for her thesis research how she does it. She is looking at gene flow from cultivated sunflowers to wild populations growing nearby fields and has made controlled pollinations between the two. She relys on the relatively strong self-incompatibility system in sunflower. She blows off as much pollen from florets that are ready on her inflorescence to serve as a female and then pollinates with the selected male and bags it. Most of the seeds should be hybrids.

If you want to play at genetics and variation it is a good idea TreeClimber16!
Sunflowers are among the most rapid growing plants with most spectacular flowers and a large variation.
All annuals are very compatible and will be bee crossed if grown close. Be they wild, agricultural or hort. vars, dwarf or giant. Every seed will be cross pollinated. Nothing easier!
Here is the difficulty if you want to select a true breeding strain... The more so if any wildlings or other plantings are not far away.
Perennials are much more complicated.

Pierre

Thanks everyone for the help.

I just want to do this for fun with my son and your help and suggestions are great.

I think we will plant one variety away from the other's to use as the female. We'll keep records and take pictures, and see what we get from the seeds the next year.

It should be fun and a great learning experience.

Sunflowers aren't too hard.
As Pierre said, most sunfloewrs are self-incompatable. That means they won't set much seed with their own pollen. I have found about 2% self-pollination in my own work.
But the commercial hybrid sunflowers have had the self-incompatiblity bred out of them. They self pollinate very easily. And any hybrid between those self-compatible hybrid sunflowers with wild or open-pollinated domestic sunflowers will have reduced self-incompatiblity.
I don't emasculate the flower I want as a seed parent. That is really hard with sunflowers. Male-sterile genes are available if you want to be sure all of your seeds are hybrids.
I collect pollen by either scraping it off the flower in mid-morning as the flower is pushing it out. I scrape it off with a popsycle stick or such thing. Or if I don't need the seeds from that flower, I pick the flower and bring it inside in a vase sitting on a piece of typing papper. the pollen falls onto the typing paper where it is easy to see and pour into a cup or something. Pollen is good for several days, but it dies immediately if it gets wet!
I use an artist paintbrush to put the pollen on the stigmas. Remember that the pollen will still live a while, so if you are making more than one cros, you need a defferent paintbrush for each kind of pollen.
The sunflower florets start to bloom from the edge of the sunflower and a ring of the florets will produce pollen the first day. the next day, the florets that produced the pollen the first day will have stigmas showing and a ring of new florets inside the ring of yesterdays florets will be producing pollen, and so on for about 3 days, maybe 4 days.
Stigmas should be pollinated about the same time the pollen is shed, or an hour or two later. They are less effective if they dry out too much. So it is morning work mostly.
Walter

Helianthus species behave rather strangely when crossed. In many cases the seedlings look completely or almost completely like the seed parent. So much so that breeders might think that the crosses didn't take. Here's a link to an article about partial hybrids in Helianthus:
http://aob.oupjournals.org/cgi/content/full/89/1/31

Hybrids of H. annuus with the sunchoke (H. tuberosus) were accomplished in the former Soviet Union. The hybrids were only weakly fertile, but after a few generations improved greatly. The results were sunflowers resistant to common sunflower diseases, and sunchokes with resistance to sunchoke diseases.

Karl King

Here is a link that might be useful: Bulb 'n' Rose

Helianthus hybrids I have made, between H. maximilianii, H. salicifolius, H. mollis, H. grosseseratus, and H. giagantus, in all combinations, gave hybrids quite intermediate between the parents.
H. occidentalis gave intermediate hybids, other than extreme hybrid vigor, with H. mollis.
In fact, it is mostly the hybrids between the cultivated H. annuus and perennials that give mostly maternal-type hybrids. And even many of the domestic H. annuus x perennials are intermediate between the species.
Those Helianthus hybrids that are most like their mothers are most likely to be fertile, when dealing with annual x perennial, though many of the hybrids do have some fertility when backcrossed repeatedly, or in large numbers.
Teh diploid annual cultivated sunflower and the Jerusalum artichoke, hexaploid, give F1 hybrids that are rather fertile when pollinated by the cultivated diploid annual. Sed set is as low as 1% or les, but with the floewr heads having large numbers of flowers, some seed can be obtained generally.
But the first backcross is triploid, as well as having different sets of chromosomes, and getting past this generaltion is hard. But when it is done, useful genes for disease resistance have been transferred to domestic sunflower. Get past the first backcross, and you have it made.
Walter

I am a Bee Grower from Israel and have 2,000 beehives. I give a pollination service for Hybriding Sunflowers and so far the results have been far from satisfactory. We put 2 beehives per acre on a 100 acre area. Can anyone help me to improve my results?